N-(3-(dimethylamino)propyl)formamide → N,N-dimethyl-N-(3-nitro-4-methoxybenzyl)-N-3-formamidopropylammonium chloride

HRID 1706098Notes

Reaction equation

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

Participants

Conditions

Temperature: 20 °C

Procedure

To a refluxing solution of 35.4 parts of N-(3-dimethylaminopropyl)formamide in 40 parts of isopropyl alcohol there was added over a two hour period 50.4 parts of 4-methoxy-3-nitrobenzyl chloride. Refluxing was continued for four hours after which the reaction mixture was diluted with 100 parts of isopropyl alcohol and cooled to 20° C. The solid that separated was collected and washed with a small amount of fresh isopropyl alcohol and then dried in a vacuum oven to yield 71.1 parts of N,N-dimethyl-N-(3-nitro-4-methoxybenzyl)-N-3-formamidopropylammonium chloride, as a cream colored solid which melted at 180°-183° C.

Workup

temperatureRefluxing
customThe solid that separated
customwas collected
washwashed with a small amount of fresh isopropyl alcohol
customdried in a vacuum oven

Sources & evidence

ORD record: ord-d28b6d54ac5440ed90ef574a6f0b80be
Source dataset: uspto-grants-1980_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04206144

Reaction notes

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