Bis(2-pyridyl) ketone → 3-Cyclohexylpropan-1-amine

HRID 378740

Reaction equation

HRID 378740 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:9]1[CH:14]=[CH:13]C=CN=1)=O>CO.C(Cl)Cl>[CH:3]1([CH2:4][CH2:5][CH2:6][NH2:1])[CH2:2][CH2:7][CH2:9][CH2:14][CH2:13]1

Participants

3

Reactant 1

HCID 88065Bis(2-pyridyl) ketone

Product 1

HCID 126663903-Cyclohexylpropan-1-amineYield 335.5%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared as above from 464.9 mg (1.11 mmol) of the pyridyl ketone and 1.00 g (2.21 mmol) of the Wittig salt. Flash chromatography with 15% MeOH-CH2Cl2 afforded 526.0 mg (92%) of the product (E/Z=~4:1 by 1H NMR): 1H NMR (DMSO) δ8.66 (s, 1H), 8.52 (m, 1H), 8.40 (dd, J=4.5, 1.1 Hz, 1H), 8.36 (d, J=1.9 Hz, 1H), 8.01 (d, J=8.2 Hz, 2H), 7.47 (m, 2H), 7.29 (d, J=8.1 Hz, 2H), 6.20 (t, J=7.4 Hz, 1H), 3.57 (br t, J=4.4 Hz, 4H), 3.28 (br dt, J=~6.2, 5.8 Hz, 2H), 2.30 (br s, 6H), 2.02 (m, 4H), 1.63 (br t, J=6.6 Hz, 2H), 1.40 (m, 4H); FDMS 519 (M+1). 97.5% pure by HPLC.

Sources & evidence

ORD record
ord-1e37e096feac46df9bee7c00e18e2e53
Source dataset
uspto-grants-2000_02
Patent number
US06031095

Linked notes

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