Methanol → Benzyl 4-amino-4-cyanopiperidine-1-carboxylate

HRID 353926Notes

Reaction equation

HRID 353926 reaction equation
[C-:1]#[N:2].[Na+].[Cl-].[NH4+:5].O=[C:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:9][CH2:8]1.CO>N>[CH2:16]([O:15][C:13]([N:10]1[CH2:11][CH2:12][C:7]([NH2:5])([C:1]#[N:2])[CH2:8][CH2:9]1)=[O:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 643496Benzyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 53217057Benzyl 4-amino-4-cyanopiperidine-1-carboxylateYield 62.8%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A solution of sodium cyanide (1052 mg, 21.5 mmol), ammonium chloride (1265 mg, 23.65 mmol), and benzyl 4-oxo-1-piperidine-carboxylate (5.0 gm, 21.5 mmol), was prepared in 5 M ammonia in methanol (8.6 mL, 43 mmol). The solution was brought to reflux for 4 h and then allowed to cool to room temperature. The solution was then filtered and washed with methanol (100 mL) and the filtrate was concentrated in vacuo. The resulting oil was taken up in MTBE (250 mL) and filtered again. The filter cake was washed with MTBE (100 mL) and the filtrate was concentrated in vacuo to yield 4-amino-4-cyano-piperidine-1-carboxylic acid benzyl ester as a clear oil (3.5 g) which was used without further purification.

Workup

  1. temperatureto reflux for 4 h
  2. filtrationThe solution was then filtered
  3. washwashed with methanol (100 mL)
  4. concentrationthe filtrate was concentrated in vacuo
  5. filtrationfiltered again
  6. washThe filter cake was washed with MTBE (100 mL)
  7. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-42a59463843a4185bf3d936d002d28ef
Source dataset
uspto-grants-2004_06
Patent number
US06756372B2

Reaction notes

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