4-Methylmorpholine → HCID 19830796, compound

HRID 569634Notes

Reaction equation

HRID 569634 reaction equation
ClC(OCC(C)C)=O.[OH:9][C:10]1[CH:11]=[CH:12][C:13]2[C:17]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=O)=[C:16]([C:29]3[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=3)[S:15][C:14]=2[CH:36]=1.CN1CCOCC1.[CH2:44]([NH2:51])[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50]>C(Cl)Cl>[CH2:44]([NH:51][C:26](=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][C:17]1[C:13]2[CH:12]=[CH:11][C:10]([OH:9])=[CH:36][C:14]=2[S:15][C:16]=1[C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 81271-HeptanamineHCID 62365Isobutyl chloroformateHCID 19830777HCID 19830777, compound

Product 1

HCID 19830796HCID 19830796, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-30 °C

Procedure

A solution of isobutyl chloroformate (0.117 g.) in methylene chloride (5 ml.) was added to a stirred solution of 9-(6-hydroxy-2-p-hydroxyphenylbenzo[b]thien-3-yl)nonanoic acid (0.1 g.) and N-methylmorpholine (0.145 g.) in methylene chloride (10 ml.) which was cooled to -30° C., and the mixture was allowed to warm up to laboratory temperature. A solution of n-heptylamine (0.098 g.) in methylene chloride (5 ml.) was added and the mixture was stirred at laboratory temperature for 1 hour and then evaporated to dryness. The residue was dissolved in methanol (5 ml.), aqueous 40% sodium hydroxide solution (2 ml.) was added and the mixture was stirred for 5 minutes and then acidified with concentrated aqueous hydrochloric acid and extracted three times with diethyl ether (20 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 100:3 v/v mixture of methylene chloride and methanol as eluant. There was thus obtained as an oil N-n-heptyl-9-(6-hydroxy-2-p-hydroxyphenylbenzo[b]thien-3-yl)nonanamide, the structure of which was confirmed by proton magnetic resonance and mass spectroscopy.

Workup

  1. temperatureto warm up to laboratory temperature
  2. customevaporated to dryness
  3. dissolutionThe residue was dissolved in methanol (5 ml.)
  4. additionaqueous 40% sodium hydroxide solution (2 ml.) was added
  5. stirringthe mixture was stirred for 5 minutes
  6. extractionextracted three times with diethyl ether (20 ml
  7. washThe combined extracts were washed with water
  8. customdried
  9. customevaporated to dryness
  10. customthe residue was purified by chromatography on a silica gel column
  11. additiona 100:3 v/v mixture of methylene chloride and methanol as eluant

Sources & evidence

ORD record
ord-26ea5b5124614bccb63a4ae20f16f601
Source dataset
uspto-grants-1988_03
Patent number
US04732912

Reaction notes

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