2-Chlorobenzylamine → N-[(2-Chlorophenyl)methyl]-1-methyl-1H-imidazo[4,5-c]pyridin-4-amine

Reaction equation

[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][N:7]=[C:6](SC)[C:5]=2[N:4]=[CH:3]1.[Cl:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][NH2:17]>>[Cl:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][NH:17][C:6]1[C:5]2[N:4]=[CH:3][N:2]([CH3:1])[C:10]=2[CH:9]=[CH:8][N:7]=1

Participants

Reactant 2

HCID 666482-Chlorobenzylamine

HCID 202107621-methyl-4-(methylthio)-1H-imidazo[4,5-c]pyridine

Product 1

HCID 13264442N-[(2-Chlorophenyl)methyl]-1-methyl-1H-imidazo[4,5-c]pyridin-4-amine

Procedure

A mixture of 17.9 of 1-methyl-4-methylthio-1H-imidazo(4,5-c)pyridine (m.p. 170°-175°) and 28 g of o-chlorobenzylamine is heated to 170°-180° for 20 hours. After cooling and customary working up, 4-o-chlorobenzylamino-1-methyl-1H-imidazo(4,5-c)pyridine of m.p. 173°-176° is obtained.

Workup

temperatureis heated to 170°-180° for 20 hours
temperatureAfter cooling

Sources & evidence

ORD record: ord-a5f9a170b2d34c46958d18a4e88a7ec8
Source dataset: uspto-grants-1987_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04654350

Reaction notes

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