Acetone → 1-Isopropyl-4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]piperidine-4-carbonitrile

HRID 273027Notes

Reaction equation

HRID 273027 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([C:22]#[N:23])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:38][C:39]([CH3:41])=O>>[CH:39]([N:19]1[CH2:18][CH2:17][C:16]([C:13]2[CH:14]=[CH:15][C:10]([O:9][CH2:8][CH2:7][CH2:6][N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:11][CH:12]=2)([C:22]#[N:23])[CH2:21][CH2:20]1)([CH3:41])[CH3:38]

Participants

4

Reactant 3

HCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 598373684-[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]piperidine-4-carbonitrile

Product 1

HCID 598373881-Isopropyl-4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]piperidine-4-carbonitrileYield 58%

Procedure

The title compound (45 mg, 58%) was prepared from 4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]piperidine-4-carbonitrile, acetone and sodium triacetoxyborohydride similarly to the procedure used for example 54. 1H NMR (400 MHz, CD3OD) 61.12 (d, 6H), 1.81-1.84 (m, 4H), 1.99-2.14 (m, 6H), 2.58-2.69 (m, 8H), 2.82 (m, 1H), 3.02 (d, 2H), 4.04 (t, 2H), 6.96 (d, 2H), 7.42 (d, 2H). HRMS ESI+ m/z 356.2691 [MH]+.

Sources & evidence

ORD record
ord-c570a10438e2478e8727f6eb0c6f2d6d
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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