Hydrochloric Acid → 4'-[4-[4-(cis-2,6-Dimethylmorpholin-4-yl)phenyl]piperazin-1-yl]-1,1'-biphenyl-4-carboxylic acid

HRID 1816756Notes

Reaction equation

HRID 1816756 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([C:23]4[CH:28]=[CH:27][C:26]([N:29]5[CH2:34][C@H:33]([CH3:35])[O:32][C@H:31]([CH3:36])[CH2:30]5)=[CH:25][CH:24]=4)[CH2:19][CH2:18]3)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+].CO.Cl>O.O1CCCC1>[CH3:35][C@H:33]1[O:32][C@@H:31]([CH3:36])[CH2:30][N:29]([C:26]2[CH:25]=[CH:24][C:23]([N:20]3[CH2:19][CH2:18][N:17]([C:14]4[CH:15]=[CH:16][C:11]([C:8]5[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=5)=[CH:12][CH:13]=4)[CH2:22][CH2:21]3)=[CH:28][CH:27]=2)[CH2:34]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 538200644'-[4-[4-(cis-2,6-Dimethylmorpholin-4-yl)phenyl]piperazin-1-yl]-1,1'-biphenyl-4-carboxylic acid methyl ester

Product 1

HCID 538355204'-[4-[4-(cis-2,6-Dimethylmorpholin-4-yl)phenyl]piperazin-1-yl]-1,1'-biphenyl-4-carboxylic acidYield 102.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4′-[4-[4-(cis-2,6-dimethylmorpholin-4-yl)phenyl]piperazin-1-yl]-1,1′-biphenyl-4-carboxylic acid methyl ester (3.70 g) and 1.0 mol/l sodium hydroxide solution (30 ml) in a mixed solvent of methanol (75 ml) and tetrahydrofuran (185 ml) was refluxed for 15.5 hours. After cooling to ambient temperature, the reaction mixture was poured into cold water, and the mixture was adjusted to pH 2 with 1.0 mol/l hydrochloric acid. The resulting precipitates were filtered, washed with water and diisopropyl ether and dried to give 4′-[4-[4-(cis-2,6-dimethylmorpholin-4-yl)phenyl]piperazin-1-yl]-1,1′-biphenyl-4-carboxylic acid (3.68 g).

Workup

  1. temperaturewas refluxed for 15.5 hours
  2. customThe resulting precipitates
  3. filtrationwere filtered
  4. washwashed with water and diisopropyl ether
  5. customdried

Sources & evidence

ORD record
ord-2ca87cb8a54e4f1c9b51de002c1fd3ba
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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