Ethyl Acetate → tert-butyl N-[(1-cyanopiperidin-4-yl)methyl]carbamate

HRID 1831801Notes

Reaction equation

HRID 1831801 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].BrC[C:24]#[N:25].C(OCC)(=O)C>C(#N)C>[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH:9]1[CH2:10][CH2:11][N:12]([C:24]#[N:25])[CH2:13][CH2:14]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamate

Product 1

HCID 23396324tert-butyl N-[(1-cyanopiperidin-4-yl)methyl]carbamate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Piperidin-4-ylmethyl-carbamic acid tert-butyl ester (4 g, 18.66 mmol) was suspended in 120 ml of acetonitrile. Dried potassium carbonate (2.837 g, 20.53 mmol) was added. A solution of bromoacetonitrile in (3.72 ml, 5 mmolar solution, 18.66 mmol) was added (argon atmosphere) and the mixture was stirred for 3 hours. After addition of aqueous FeSO4 solution and ethyl acetate, the separated solid was filtered and the organic layer separated, dried and evaporated.

Workup

  1. filtrationthe separated solid was filtered
  2. customthe organic layer separated
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-724c546b1ff04290aeae174fc648cf90
Source dataset
uspto-grants-2006_06
Patent number
US07067665B2

Reaction notes

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