Acetic Acid → 1-(Cyclopropylamino)cycloheptanecarbonitrile

HRID 1092351Notes

Reaction equation

HRID 1092351 reaction equation
[C:1]1(=O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C-:9]#[N:10].[K+].[CH:12]1([NH2:15])[CH2:14][CH2:13]1.C(O)(=O)C>CO>[CH:12]1([NH:15][C:1]2([C:9]#[N:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 9032Potassium CyanideHCID 10400CycloheptanoneHCID 69828Cyclopropylamine

Product 1

HCID 431516641-(Cyclopropylamino)cycloheptanecarbonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5 g (44.57 mmol) of Cycloheptanone and 4.1 g of potassium cyanide were added to a solution of 4.38 ml (62.4 mmol) cyclopropylamine and 3.56 ml (62.4 mmol) of acetic acid in 50 ml MeOH. The reaction-mixture was stirred for 24 h, and then it was concentrated under reduced pressure, taken up in EtOAc and washed with water. The organic layer was concentrated under reduced pressure to give 6.84 g almost pure 1-Cyclopropylamino-cycloheptanecarbonitrile. MS (ESI): 179.3 (M+H)

Workup

  1. concentrationit was concentrated under reduced pressure
  2. washwashed with water
  3. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cfbe75cc3f02459aa6b7761b9174d8fc
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

Loading…