Hydrochloric Acid → 2,6-Dimethyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid N-[3-(4,4-diphenylpiperidin-1-yl)propyl]amide methyl ester hydrochloride hydrate

HRID 1901515Notes

Reaction equation

HRID 1901515 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:37]2[CH:42]=[CH:41][C:40]([N+:43]([O-:45])=[O:44])=[CH:39][CH:38]=2)[C:7]([C:13]([NH:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][C:22]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:21][CH2:20]2)=[O:14])=[C:8]([CH3:12])[NH:9][C:10]=1[CH3:11])=[O:4].[ClH:46].CCOCC.C(OCC)(=O)C>CCO>[OH2:2].[ClH:46].[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:37]2[CH:38]=[CH:39][C:40]([N+:43]([O-:45])=[O:44])=[CH:41][CH:42]=2)[C:7]([C:13]([NH:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:20][CH2:21][C:22]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:23][CH2:24]2)=[O:14])=[C:8]([CH3:12])[NH:9][C:10]=1[CH3:11])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 8857Ethyl AcetateHCID 98090073-Pyridinecarboxylic acid, 5-[[[3-(4,4-diphenyl-1-piperidinyl)propyl]amino]carbonyl]-1,4-dihydro-2,6-dimethyl-4-(4-nitrophenyl)-, methyl ester

Product 1

HCID 699658542,6-Dimethyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid N-[3-(4,4-diphenylpiperidin-1-yl)propyl]amide methyl ester hydrochloride hydrate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,6-dimethyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid N-[3-(4,4-diphenylpiperidin-1-yl)propyl]amide methyl ester (147.8 mg, 0.243 mmol, 1.0 equiv) in EtOH (2 mL) was added a solution of HCl in ether (1.0M, 0.24 mL, 0.24 mmol, 1.0 equiv). Addition of ethyl acetate (3 mL) followed by heating gave a clear solution. Slow cooling of this solution, followed by filtration gave 91 mg of yellow crystalline solid: m.p. 182°-183° C.; Anal. Calcd. for C36H40N4O5 ·HCI·H2O: C, 65.20, H, 6.54; N, 8.45. Found: C, 65.30; H, 6.28; N, 8.15.

Workup

  1. temperatureby heating
  2. customgave a clear solution
  3. temperatureSlow cooling of this solution
  4. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-03488502fbf74bb9a246ee640e898ae5
Source dataset
uspto-grants-1996_11
Patent number
US05578611

Reaction notes

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