Acetic Acid → 4-methyl-7-Dimethylamino-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione

HRID 1844297Notes

Reaction equation

[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[CH:10]=[C:11](N)[CH:12]=[CH:13][C:6]=2[NH:5][C:4](=[O:15])[CH2:3]1.C=O.[BH3-][C:19]#[N:20].[Na+].[C:22](O)(=O)C>C(#N)C.C(OCC)C>[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[CH:10]=[C:11]([N:20]([CH3:19])[CH3:22])[CH:12]=[CH:13][C:6]=2[NH:5][C:4](=[O:15])[CH2:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of intermediate 3 (3.0 g, 13 mmol) and 37% aq formaldehyde (21 mL, 0.26 mol) in acetonitrile at 0° C., NaBH3CN (4.8 g, 77 mmol) was added portionwise. The reaction mixture was stirred at 0° C. for 2 h and then at room temperature for 1 h. Acetic acid (1.4 mL) was then added and the reaction mixture was stirred for another 2 h. The reaction mixture was poured into ethyl ether, washed with 2N KOH and the basic layer was extracted several times with ethyl acetate. The organic phases were collected and dried and solvents removed in vacuum to give an amorphous yellowish solid.

Workup

waitat room temperature for 1 h
stirringthe reaction mixture was stirred for another 2 h
washwashed with 2N KOH
extractionthe basic layer was extracted several times with ethyl acetate
customThe organic phases were collected
customdried
customsolvents removed in vacuum
customto give an amorphous yellowish solid

Sources & evidence

ORD record: ord-58f30c58fb134e38a5b4a8f842dca89c
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946410B2

Reaction notes

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