4-Cyanopiperidine → HCID 57993257, compound

HRID 508630Notes

Reaction equation

HRID 508630 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-f69473575abe4aeeb8fe8b31ce4cdb63
Source dataset
uspto-grants-2015_08
Patent number
US09096522B2

Reaction notes

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