4-Cyanopiperidine → HCID 57993257, compound

HRID 388770Notes

Reaction equation

HRID 388770 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]#[N:8])[CH2:3][CH2:2]1.O=[CH:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[C:7]([CH:4]1[CH2:5][CH2:6][N:1]([CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:2][CH2:3]1)#[N:8]

Participants

5

Reactant 3

HCID 1382234-CyanopiperidineHCID 4247255tert-butyl N-(2-oxoethyl)carbamateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 57993257HCID 57993257, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of piperidine-4-carbonitrile (1.10 g, 10 mmol), tert-butyl 2-oxoethylcarbamate (1.59 g, 10 mmol) and sodium triacetoxy borohydride (2.5 g, 12 mmol) in 25 ml of CH2Cl2 was stirred at room temperature overnight. Solvent was evaporated and ethyl acetate was added and washed with water. The solvent was removed in vacuo to provide oil. The crude oil was purified by column chromatography (100% ethyl acetate) to yield colorless oil (2.3 g, 91%).

Workup

  1. customSolvent was evaporated
  2. additionethyl acetate was added
  3. washwashed with water
  4. customThe solvent was removed in vacuo
  5. customto provide oil
  6. customThe crude oil was purified by column chromatography (100% ethyl acetate)

Sources & evidence

ORD record
ord-e460e2b5178d4a429d4cf860820dbd7a
Source dataset
uspto-grants-2013_02
Patent number
US08377968B2

Reaction notes

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