Chloroacetonitrile → 1-(Cyanomethyl)-3-methoxy-3-[3-(naphth-2-ylmethoxy)phenyl]pyrrolidine

HRID 37553Notes

Reaction equation

[CH3:1][O:2][C:3]1([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=3)[CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4]1.Cl[CH2:27][C:28]#[N:29]>>[C:28]([CH2:27][N:5]1[CH2:6][CH2:7][C:3]([O:2][CH3:1])([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=3)[CH:9]=2)[CH2:4]1)#[N:29]

Participants

Reactant 2

HCID 7856Chloroacetonitrile

HCID 19935823HCID 19935823, compound

Product 1

HCID 199358111-(Cyanomethyl)-3-methoxy-3-[3-(naphth-2-ylmethoxy)phenyl]pyrrolidineYield 45%

Procedure

Using an analogous procedure to that described in Example 3, 3-methoxy-3-[3-(naphth-2-ylmethoxy)phenyl]pyrrolidine was reacted with 2-chloroacetonitrile to give 1-(cyanomethyl)-3-methoxy-3-[3-(naphth-2-ylmethoxy)phenyl]pyrrolidine in 45% yield, m.p. 76°-77° C. (recrystallised from methanol).

Sources & evidence

ORD record: ord-988c8deec7924439a3156a6a3fc332c9
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05420298

Reaction notes

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