2-(Dimethylamino)-2-methylbutanenitrile → (+/-){1-[Amino(phenyl)methyl]-1-methylpropyl}dimethylamine

HRID 20805Notes

Reaction equation

HRID 20805 reaction equation
[CH3:1][N:2]([CH3:9])[C:3]([CH3:8])([CH2:6][CH3:7])[C:4]#[N:5].[C:10]1([Li])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[BH4-].[Na+].CC(N1CCCC1)(C)C(N)C1C=CC=CC=1>C(OCCCC)CCC.C1COCC1.CO>[NH2:5][CH:4]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3]([N:2]([CH3:9])[CH3:1])([CH3:8])[CH2:6][CH3:7]

Participants

8

Reactant 4

HCID 2333942-(Dimethylamino)-2-methylbutanenitrileHCID 4311764Sodium borohydrideHCID 25158607[2-Methyl-1-phenyl-2-(1-pyrrolidinyl)propyl]amineHCID 178506676HCID 178506676, compound

Product 1

HCID 59347825(+/-){1-[Amino(phenyl)methyl]-1-methylpropyl}dimethylamineYield 93%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8909Butyl etherSolvent

Procedure

The title compound (15 g, 93%) was prepared from 2-(dimethylamino)-2-methylbutanenitrile D23 (9.9 g, 0.078 mol) and phenyllithium in dibutylether (87.3 ml of a 1.8M solution; 0.157 mol) in THF (400 ml), followed by reaction with sodium borohydride (5.25 g, 0.138 mol) in methanol (450 ml) in a similar manner to that described in D5. Mass spectrum (Electrospray LC/MS), ES+: Found 207 (MH+). C13H22N2 requires 206. Ret. times 0.83 and 1.10 min.

Workup

  1. customtimes 0.83 and 1.10 min.

Sources & evidence

ORD record
ord-885084acbd6445d6a1f148aaa66061aa
Source dataset
uspto-grants-2010_06
Patent number
US07745642B2

Reaction notes

Loading…