Benzonitrile, 3-(bromomethyl)- → Methylamine

HRID 1244562Notes

Reaction equation

HRID 1244562 reaction equation
COC(C1CC(=O)[N:7](C2C=CC(O)=CC=2)[CH2:6]1)=O.[C:18](C1C=C(C=CC=1)CBr)#[N:19].CO[C:30]([CH:32]1[CH2:36][C:35](=[O:37])[N:34]([C:38]2[CH:43]=[CH:42][C:41]([O:44][CH2:45][C:46]3[CH:51]=[CH:50][CH:49]=[C:48]([C:52]#[N:53])[CH:47]=3)=[CH:40][CH:39]=2)[CH2:33]1)=[O:31]>C(O)C>[CH3:6][NH2:7].[CH3:18][NH:19][C:30]([CH:32]1[CH2:36][C:35](=[O:37])[N:34]([C:38]2[CH:43]=[CH:42][C:41]([O:44][CH2:45][C:46]3[CH:51]=[CH:50][CH:49]=[C:48]([C:52]#[N:53])[CH:47]=3)=[CH:40][CH:39]=2)[CH2:33]1)=[O:31]

Participants

6

Reactant 3

HCID 97249Benzonitrile, 3-(bromomethyl)-HCID 2883518Methyl 1-(4-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylateHCID 86592633HCID 86592633, compound

Product 2

HCID 6329MethylamineHCID 10450478HCID 10450478, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound is prepared by alkylation of the (RS)-1-(4-hydroxyphenyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester with 3-cyanobenzyl bromide giving the (RS)-1-[4-(3-cyano-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methylester as a light yellow solid [69% of theory, MS: m/e=351 (M+H)+] which, thereupon, by treatment with methylamine in ethanol at 80° C. yields the (RS)-1-[4-(3-cyano-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methylamide. Yield: 79% of theory as a white powder. MS: m/e=350 (M+H)+.

Sources & evidence

ORD record
ord-e61d9998cf964118a15dfd5de1791ee0
Source dataset
uspto-grants-2006_10
Patent number
US07122562B2

Reaction notes

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