Hydrochloric Acid → tert-Butyl 4-{[3'-(aminomethyl)biphenyl-3-yl]methyl}piperidine-1-carboxylate

HRID 657375Notes

Reaction equation

HRID 657375 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].Cl>CO.[OH-].[OH-].[Pd+2]>[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

5

Reactant 2

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

Product 1

HCID 57813360tert-Butyl 4-{[3'-(aminomethyl)biphenyl-3-yl]methyl}piperidine-1-carboxylateYield 95.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst4×HCID 887MethanolSolvent

Procedure

1,1-Dimethylethyl 4-[(3′-cyano-3-biphenylyl)methylidene]-1-piperidinecarboxylate (0.517 g, 1.381 mmol) in methanol (138 mL) was applied to H-Cube hydrogenation apparatus. This resultant mixture was run with a Pd(OH)2 cartridge at 1 mL/min, with 1 atmosphere at 20° C. HCl (1.38 mL, 1 N) was then added. One portion was run one time with Pd(OH)2 cartridge at 1 mL/min, 1 atmosphere at 20° C. Another portion was run with 1 run, Pd(OH)2 cartridge at 1 mL/min with 50 atmosphere and 20° C. Both portions were combined for 1 run, Pd(OH)2 cartridge, 1 mL/min with 1 atmosphere at 20° C. The reaction mixture was concentrated to afford the title compound (0.501 g, 87%). LC-MS m/z 381 (M+H)+.

Workup

  1. customat 20° C
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-9f475ccb43764a63baebd6019f212550
Source dataset
uspto-grants-2011_12
Patent number
US08071588B2

Reaction notes

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