Cyclohexanone → HCID 59347798, compound

HRID 20822Notes

Reaction equation

HRID 20822 reaction equation
Cl.CNC.[C:5]1(=O)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[C-]#N.[K+].CN(C)C1(C#N)CCCC1.[CH3:25][N:26]([CH3:35])[C:27]1([C:33]#[N:34])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.C1([Li])C=CC=CC=1.[BH4-].[Na+].NC(C1C=CC=CC=1)C1(N(C)C)CCCC1>O.C(OCCCC)CCC.C1COCC1>[NH2:34][CH:33]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:27]1([N:26]([CH3:35])[CH3:25])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

12

Reactant 8

HCID 7967CyclohexanoneHCID 9032Potassium CyanideHCID 10473Dimethylamine, hydrochlorideHCID 1011881-(Dimethylamino)cyclohexanecarbonitrileHCID 4311764Sodium borohydrideHCID 107730491-(Dimethylamino)cyclopentanecarbonitrileHCID 11521393{1-[Amino(phenyl)methyl]cyclopentyl}dimethylamineHCID 178506676HCID 178506676, compound

Product 1

HCID 59347798HCID 59347798, compoundYield 36%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8909Butyl etherSolvent

Procedure

The title compound was prepared in two stages from (i) dimethylamine hydrochloride (3.26 g, 0.04 mol), cyclohexanone (3.9 g, 0.04 mol) and potassium cyanide (2.60 g, 0.04 mol) in water (25 ml) in a similar manner to that described in D1 to make 1-(dimethylamino)cyclohexanecarbonitrile (6.6 g, 100%). This was reacted directly in (ii) with phenyl lithium in dibutyl ether (10.5 ml of a 1.9M solution, 0.02 mol) in THF (30 ml) followed by sodium borohydride (1.51 g, 0.04 mol) in a similar manner to that described in D2 to afford the title compound (2.5 g, 36%). 1H NMR (CDCl3) δ: 0.85 (1H, m), 1.00 (1H, m), 1.25 (2H, m), 1.35-1.60 (6H, br m), 1.70 (1H, m), 2.10 (1H, m), 2.46 (6H, s), 4.15 (1H, s), 7.20-7.32 (5H, m).

Sources & evidence

ORD record
ord-9c53447d44cc4e7e8f74a8e8f8979bc9
Source dataset
uspto-grants-2010_06
Patent number
US07745642B2

Reaction notes

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