Formaldehyde → 1-Methyl-4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]piperidine-4-carbonitrile

HRID 273026Notes

Reaction equation

HRID 273026 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.[C:26](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH3:26][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

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 598373684-[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]piperidine-4-carbonitrile

Product 1

HCID 598374231-Methyl-4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]piperidine-4-carbonitrileYield 76%

Procedure

The title compound (80 mg, 76%) was prepared from 4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]piperidine-4-carbonitrile, formaldehyde and sodium triacetoxyborohydride similarly to the procedure used for example 54. 1H NMR (400 MHz, CD3OD) δ 1.81-1.85 (m, 4H), 1.97-2.15 (m, 6H), 2.37 (s, 3H), 2.45 (t, 2H), 2.58-2.62 (m, 4H), 2.68 (t, 2H), 2.99 (d, 2H), 4.04 (t, 2H), 6.96 (d, 2H), 7.42 (d, 2H). LRMS APCI+ m/z 328 [MH]+. Microanalysis: Found: C, 73.01; H, 8.94; N, 12.81%. C20H29N3O requires C, 73.36; H, 8.93; N, 12.83%.

Sources & evidence

ORD record
ord-05245105edc54e7eb07bf7a25ae8543f
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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