2-Methyl-2-piperidin-1-ylpropanenitrile → (+/-)2-Methyl-1-phenyl-2-(1-piperidinyl)-1-propanamine

HRID 20789

Reaction equation

HRID 20789 reaction equation
[CH3:1][C:2]([N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)([CH3:5])[C:3]#[N:4].[C:12]1([Li])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[BH4-].[Na+].NC(C1C=CC=CC=1)C1(N(C)C)CCCC1>C(OCCCC)CCC.C1COCC1.CO>[CH3:5][C:2]([N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)([CH3:1])[CH:3]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[NH2:4]

Participants

8

Reactant 4

HCID 2888822-Methyl-2-piperidin-1-ylpropanenitrileHCID 4311764Sodium borohydrideHCID 11521393{1-[Amino(phenyl)methyl]cyclopentyl}dimethylamineHCID 178506676HCID 178506676, compound

Product 1

HCID 199304(+/-)2-Methyl-1-phenyl-2-(1-piperidinyl)-1-propanamineYield 56%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8909Butyl etherSolvent

Procedure

The title compound (1.16 g, 56%) was prepared from 2-methyl-2-(1-piperidinyl)propanenitrile D7 (1.30 g, 8.6 mmol), and phenyllithium in dibutylether (5.2 ml of a 1.8M solution; 9.4 mmol) in THF (15 ml), followed by reaction with sodium borohydride (0.975 g, 25.7 mmol) in methanol (20 ml) in a similar manner to that described in D2. 1H NMR (CDCl3) δ: 0.76 (3H, s), 0.91 (3H, s), 1.44 (2H, m), 1.54-1.65 (4H, m), 1.95 (2H, m), 2.57 (4H, m), 4.19 (1H, s), 7.20-7.31 (3H, m), 7.40 (2H, m).

Sources & evidence

ORD record
ord-246ca7faebb947818f80c9620a83e184
Source dataset
uspto-grants-2010_06
Patent number
US07745642B2

Linked notes

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