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

HRID 20809
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HRID 20809 반응식
[CH3:1][N:2]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)C1(C#N)CCCC1.C1([Li])C=CC=CC=1.C(OCCCC)CCC.[BH4-].[Na+].[NH2:35][CH:36]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:37]1(N(C)C)[CH2:41][CH2:40][CH2:39][CH2:38]1>C1COCC1.CO>[NH2:35][CH:36]([C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)[C:37]1([CH2:1][NH:2][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:38][CH2:39][CH2:40][CH2:41]1
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참가 물질

8

반응물 5

HCID 8909Butyl etherHCID 4311764Sodium borohydrideHCID 11521393{1-[Amino(phenyl)methyl]cyclopentyl}dimethylamineHCID 215815441-[Methyl(phenylmethyl)amino]cyclopentanecarbonitrileHCID 178506676HCID 178506676, 화합물

생성물 1

HCID 68837670(+/-)-{1-[Amino(phenyl)methyl]cyclopentyl}methyl (phenylmethyl) amine
수율 47%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

The title compound (3.90 g; 47%) was prepared from 1-[methyl(phenylmethyl)amino]cyclopentanecarbonitrile D28 (6.0 g; 28 mmol) and phenyllithium in di-n-butylether (16.21 ml of 1.9M solution; 30.8 mmol) in THF (60 ml), followed by reaction with sodium borohydride (3.2 g; 84 mmol) in methanol (60 ml) in a similar manner to that described in D2. Mass Spectrum (Electrospray LC/MS), API+: Found 295 (MH+). C20H26N2 requires 294. Ret. time 2.12 min.

출처 및 근거

ORD 기록
ord-1fb988fc9adb4ceeaad621b801b09955
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07745642B2

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