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1-(1-Pyrrolidinyl)cyclopentanecarbonitrile → (+/-)1-Phenyl-1-[1-(1-pyrrolidinyl)cyclopentyl]methanamine

HRID 20791
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HRID 20791 반응식
[N:1]1([C:6]2([C:11]#[N:12])[CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:13]1([Li])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[BH4-].[Na+].NC(C1C=CC=CC=1)C1(N(C)C)CCCC1>C(OCCCC)CCC.C1COCC1.CO>[C:13]1([CH:11]([C:6]2([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[CH2:7][CH2:8][CH2:9][CH2:10]2)[NH2:12])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1
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참가 물질

8

반응물 4

HCID 5863471-(1-Pyrrolidinyl)cyclopentanecarbonitrileHCID 4311764Sodium borohydrideHCID 11521393{1-[Amino(phenyl)methyl]cyclopentyl}dimethylamineHCID 178506676HCID 178506676, 화합물

생성물 1

HCID 59347883(+/-)1-Phenyl-1-[1-(1-pyrrolidinyl)cyclopentyl]methanamine수율 56%

시약·촉매·용매 3

HCID 887
Methanol
용매
HCID 8028Tetrahydrofuran용매
HCID 8909Butyl ether용매

실험 절차

The title compound (0.55 g, 56%) was prepared from 1-(1-pyrrolidinyl)cyclopentane carbonitrile D9 (0.66 g, 4 mmol), and phenyllithium in dibutylether (2.4 ml of a 1.8M solution; 4.4 mmol) in THF (4 ml), followed by reaction with sodium borohydride (0.456 g, 12 mmol) in methanol (4 ml) in a similar manner to that described in D2. 1H NMR (CDCl3) δ: 0.41 (1H, m), 1.17 (1H, m), 1.35 (2H, m), 1.60 (2H, m), 1.73 (5H, m), 1.84-2.02 (3H, m), 2.64-2.74 (4H, m), 4.27 (1H, s), 7.21-7.31 (3H, m), 7.48 (2H, m).

출처 및 근거

ORD 기록
ord-ff49f2d023844b15b2922272e5af7878
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07745642B2

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