Sodium hydride → N-[4-[(6,11-Dihydro-5H-dibenz[b,e]azepin-5-yl)carbonyl]phenyl]-N-[(dimethylamino)methyl]-2-methylbenzamide

HRID 1938316Notes

Reaction equation

HRID 1938316 reaction equation
[H-].[Na+].[CH:3]1[C:13]2[CH2:12][C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[CH2:9][N:8]([C:18]([C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:35])[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[CH3:34])=[CH:22][CH:21]=3)=[O:19])[C:7]=2[CH:6]=[CH:5][CH:4]=1.[I-].[CH3:37][N+:38](=[CH2:40])[CH3:39]>O1CCCC1.CCOCC>[CH:3]1[C:13]2[CH2:12][C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[CH2:9][N:8]([C:18]([C:20]3[CH:25]=[CH:24][C:23]([N:26]([CH2:37][N:38]([CH3:40])[CH3:39])[C:27](=[O:35])[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[CH3:34])=[CH:22][CH:21]=3)=[O:19])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 2724133Dimethyl(methylene)ammounium iodideHCID 15307968N-[4-(6,11-Dihydro-dibenzo[b,e]azepine-5-carbonyl)-phenyl]-2-methyl-benzamide

Product 1

HCID 44212558N-[4-[(6,11-Dihydro-5H-dibenz[b,e]azepin-5-yl)carbonyl]phenyl]-N-[(dimethylamino)methyl]-2-methylbenzamideYield 88.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 14 mg of 60% sodium hydride in oil, in 2 ml of tetrahydrofuran is added 0.13 g of N-[4-[(6,11-dihydro-5H-dibenz[b,e]azepin-5-yl)carbonyl]phenyl]-2-methylbenzamide. The reactants are stirred for 1 hour and 62 mg of N,N-dimethyl-methylene ammonium iodide added followed by stirring for 2 hours. The mixture is diluted with 10 ml of ether and filtered. The filtrate is evaporated in vacuo to a residue which is stirred with hexanes to give 0.13 g of the desired product as a white solid, m.p. 131°-133° C.

Workup

  1. stirringby stirring for 2 hours
  2. filtrationfiltered
  3. customThe filtrate is evaporated in vacuo to a residue which
  4. stirringis stirred with hexanes

Sources & evidence

ORD record
ord-d2c7bf5d80c741fea679ee21f221b4a4
Source dataset
uspto-grants-1997_12
Patent number
US05693635

Reaction notes

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