Hydrochloric Acid → HCID 54316643, compound

HRID 2290476Notes

Reaction equation

HRID 2290476 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH2:15]([N:31]1[CH2:36][CH2:35][N:34]([C:37]2[CH:42]=[CH:41][C:40]([CH:43](O)[CH2:44][C:45]([O:47]C)=[O:46])=[CH:39][CH:38]=2)[CH2:33][CH2:32]1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C(N1CCN(C2C=CC(C(=O)CC(OC)=O)=CC=2)CC1)CCCCCCCCCCCCCCC.[BH4-].[Na+].Cl>CO.C(Cl)Cl>[CH2:15]([N:31]1[CH2:36][CH2:35][N:34]([C:37]2[CH:42]=[CH:41][C:40]([CH:43]=[CH:44][C:45]([OH:47])=[O:46])=[CH:39][CH:38]=2)[CH2:33][CH2:32]1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14812Phosphorus oxide (P4O10)HCID 4311764Sodium borohydrideHCID 20232629HCID 20232629, compoundHCID 20232677HCID 20232677, compound

Product 1

HCID 54316643HCID 54316643, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

6.81 g. (48 mmole) Phosphorus pentoxide are suspended in 100 ml. methylene chloride, 15.2 g. (32 mmole) methyl 3-{4-[1-(n-hexadecyl)-piperazin-4-yl]-phenyl}-3-hydroxypropionate (colourless oil, prepared by the reduction of methyl 3-{4-[1-(n-hexadecyl)-piperazin-4-yl]-phenyl}-3-oxopropionate with sodium borohydride in methanol) are added thereto and the mixture is heated, with vigorous stirring, for 12 hours at reflux temperature. Subsequently, the smeary polyphosphoric acid is separated by decantation, the liquid phase is evaporated, the evaporation residue is dissolved in ethanol and, after the addition of 50 ml. 2N aqueous potassium hydroxide solution, the mixture is heated for 6 hours to 85° C. Subsequently, the ethanol is distilled off, the aqueous phase is extracted with diethyl ether and thereafter acidified with 6N hydrochloric acid. The precipitated product is filtered off with suction, washed with cold 2N hydrochloric acid and dried to give 8.8 g. (56% of theory) of the hydrochloride of the desired compound; m.p. 251°-253° C.

Workup

  1. additionare added
  2. temperaturethe mixture is heated, with vigorous stirring, for 12 hours
  3. temperatureat reflux temperature
  4. customSubsequently, the smeary polyphosphoric acid is separated by decantation
  5. customthe liquid phase is evaporated
  6. dissolutionthe evaporation residue is dissolved in ethanol
  7. additionafter the addition of 50 ml
  8. temperature2N aqueous potassium hydroxide solution, the mixture is heated for 6 hours to 85° C
  9. distillationSubsequently, the ethanol is distilled off
  10. extractionthe aqueous phase is extracted with diethyl ether
  11. filtrationThe precipitated product is filtered off with suction
  12. washwashed with cold 2N hydrochloric acid
  13. customdried
  14. customto give 8.8 g

Sources & evidence

ORD record
ord-913abe39459044269739fef3422c7ef7
Source dataset
uspto-grants-1986_10
Patent number
US04616086

Reaction notes

Loading…