Hydrochloric Acid → 1,1-Dimethylethyl 4-{[3'-(aminomethyl)-3-biphenylyl]methyl}-1-piperidinecarboxylate Hydrochloride

HRID 564569Notes

Reaction equation

HRID 564569 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=[C:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)[CH:10]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].[ClH:29]>CO>[ClH:29].[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)[CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 670058691,1-Dimethylethyl 4-[(3'-cyano-3-biphenylyl)methylidene]-1-piperidinecarboxylate

Product 1

HCID 670057291,1-Dimethylethyl 4-{[3'-(aminomethyl)-3-biphenylyl]methyl}-1-piperidinecarboxylate HydrochlorideYield 67.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1,1-dimethylethyl 4-[(3′-cyano-3-biphenylyl)methylidene]-1-piperidinecarboxylate (1.87 g, 4.99 mmol) in MeOH (499 mL) was added HCl (4.99 mL, 1N, 4.99 mmol) then was applied to H-cube hydrogenation apparatus until the reaction was complete per monitoring with LC-MS. The reaction mixture was concentrated to afford 1.40 g (67%) of the title compound. LC-MS m/z 381 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-35dc5d4853484091a897b484caf7b90c
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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