Butyl ether → (+/-){1-[Amino(phenyl)methyl]cyclopentyl}bis(phenylmethyl)amine

HRID 20812Notes

Reaction equation

HRID 20812 reaction equation
[C:1]1([CH2:7][N:8]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]2([C:14]#[N:15])[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:23]1([Li])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(OCCCC)CCC.[BH4-].[Na+].NC(C1C=CC=CC=1)C1(N(C)C)CCCC1>C1COCC1.CO>[NH2:15][CH:14]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:9]1([N:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

8

Reactant 5

HCID 8909Butyl etherHCID 4311764Sodium borohydrideHCID 11521393{1-[Amino(phenyl)methyl]cyclopentyl}dimethylamineHCID 593477851-[Bis(phenylmethyl)amino]cyclopentanecarbonitrileHCID 178506676HCID 178506676, compound

Product 1

HCID 59347885(+/-){1-[Amino(phenyl)methyl]cyclopentyl}bis(phenylmethyl)amineYield 38%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound (2.31 g; 38%) was prepared from 1-[bis(phenylmethyl)amino]cyclopentanecarbonitrile D32 (4.0 g; 13.8 mmol), and phenyllithium in di-n-butylether (8.4 ml of 1.8M solution; 15.2 mmol) in THF (80 ml), followed by reaction with sodium borohydride (1.57 g; 41.4 mmol) in methanol (80 ml) in a similar manner to that described in D2. Mass Spectrum (Electrospray LC/MS), API+: Found 371 (MH+). C26H30N2 requires 370. Ret. time 2.62 min.

Sources & evidence

ORD record
ord-74bd9055a99f41b88ad3c0ce816330ab
Source dataset
uspto-grants-2010_06
Patent number
US07745642B2

Reaction notes

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