N,N-Dimethylaniline → HCID 9799174, compound

HRID 2244215Notes

Reaction equation

HRID 2244215 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[NH:7][CH2:6][C:5]=12.CN(C)C1C=CC=CC=1.[C:24]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:29]=[CH:28][C:27]([C:30](Cl)=[O:31])=[CH:26][CH:25]=1.O>O1CCOCC1>[C:24]1([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:25]=[CH:26][C:27]([C:30]([N:7]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH2:10][N:4]3[CH:3]=[CH:2][CH:1]=[C:5]3[CH2:6]2)=[O:31])=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 962WaterHCID 841514-Phenylbenzoyl chlorideHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine

Product 1

HCID 9799174HCID 9799174, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5.53 g (0.03 mol) of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 50 mL of 1,4-dioxane was added 3.64 g (0.03 mol) of N,N-dimethylaniline followed by 6.50 g. of 4-biphenylcarbonyl chloride. The reaction solution was allowed to stand at room temperature for 2 hours and then slowly poured into 2 L of water. On cooling the mixture a crystalline white solid was formed which was collected and dried to provide the title compound (9.5 g). The product was used directly in the next step.

Workup

  1. temperatureOn cooling the mixture a crystalline white solid
  2. customwas formed which
  3. customwas collected
  4. customdried

Sources & evidence

ORD record
ord-9628790b887541ddb1efed3c326248f0
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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