Hydrochloric Acid → HCID 54227644, compound

HRID 1493293Notes

Reaction equation

HRID 1493293 reaction equation
ClC(OCC(C)C)=[O:3].C[O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[C:17]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]CC(O)=O)=[C:16]([C:34]1[CH:39]=[CH:38][C:37]([O:40]C)=[CH:36][CH:35]=1)[CH:15]=[CH:14]2.[CH3:42][N:43]1[CH2:48][CH2:47]O[CH2:45][CH2:44]1.CNCC[CH2:53][CH3:54].Cl>C(Cl)Cl.O>[CH2:48]([N:43]([CH3:42])[C:44](=[O:3])[CH2:45][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][C:17]1[C:18]2[C:13](=[CH:12][C:11]([OH:10])=[CH:20][CH:19]=2)[CH:14]=[CH:15][C:16]=1[C:34]1[CH:35]=[CH:36][C:37]([OH:40])=[CH:38][CH:39]=1)[CH2:47][CH2:53][CH3:54]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 8068N-MethylbutylamineHCID 62365Isobutyl chloroformateHCID 54266849HCID 54266849, compound

Product 1

HCID 54227644HCID 54227644, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-30 °C

Procedure

A solution of isobutyl chloroformate (0.09 g.) in methylene chloride (5 ml.) was added to a stirred solution of 11-(6-methoxy-2-p-methoxyphenylnaphth-1-yl)undecanoic acid (0.25 g.) and -N-methylmorpholine (0.17 g.) in methylene chloride (10 ml.) which was cooled to -30° C., and the mixture was allowed to warm up laboratory temperature. A solution N-methylbutylamine (0.073 g.) in methylene chloride (5 ml.) was added and the mixture was stirred for 2 hours, neutralised with aqueous 2N-hydrochloric acid (15 ml.) and extracted three times with diethyl ether (30 ml. each time). The combined extracts were washed with water, dried and evaporated to dryness and the residue was purified by chromatography on a silica gel column using a 100:1 v/v mixture of methylene chloride and methanol as eluant. A solution of boron tribromide (0.48 g.) in methylene chloride (3 ml.) was added to a stirred solution of the N-butyl-11-(6-methoxy-2-p-methoxyphenylnaphth-1-yl)-N-methylundecanamide thus obtained (0.2 g.) in methylene chloride (10 ml.) which was cooled to -30° C. under an atmosphere of argon, and the mixture was allowed to warm up to 0° C. and was stirred at that temperature for 2 hours. Water (10 ml.) was added, the mixture was extracted three times with diethyl ether (20 ml. each time) and the combined extracts were washed with water, dried and evaporated to dryness. The residue was purified by chromatography on a silica gel column using a 100:3 v/v mixture of methylene chloride and methanol as eluant. There was thus obtained as an oil N-butyl-11-(6-hydroxy-2-p-hydroxyphenylnaphth-1-yl)-N-methylundecanamide, the structure of which was confirmed by proton magnetic resonance and mass spectroscopy as follows:

Workup

  1. temperatureto warm up laboratory temperature
  2. extractionextracted three times with diethyl ether (30 ml
  3. washThe combined extracts were washed with water
  4. customdried
  5. customevaporated to dryness
  6. customthe residue was purified by chromatography on a silica gel column
  7. additiona 100:1 v/v mixture of methylene chloride and methanol as eluant
  8. additionA solution of boron tribromide (0.48 g.) in methylene chloride (3 ml.) was added to a stirred solution of the N-butyl-11-(6-methoxy-2-p-methoxyphenylnaphth-1-yl)-N-methylundecanamide
  9. customthus obtained (0.2 g.) in methylene chloride (10 ml.) which
  10. temperatureto warm up to 0° C.
  11. stirringwas stirred at that temperature for 2 hours
  12. extractionthe mixture was extracted three times with diethyl ether (20 ml
  13. washeach time) and the combined extracts were washed with water
  14. customdried
  15. customevaporated to dryness
  16. customThe residue was purified by chromatography on a silica gel column
  17. additiona 100:3 v/v mixture of methylene chloride and methanol as eluant

Sources & evidence

ORD record
ord-09e4be55870b4b4c8a9708820869ee53
Source dataset
uspto-grants-1991_06
Patent number
US05021414

Reaction notes

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