Dimethylformamide → HCID 67264680, compound

HRID 1687928Notes

Reaction equation

HRID 1687928 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:11][CH2:10][CH2:9][C:8]([CH3:13])([CH3:12])[C:7]2[CH:14]=[CH:15][C:16]([N+:18]([O-:20])=[O:19])=[CH:17][C:6]1=2)=[O:4].[NH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1.CN(C)C=O>>[CH3:12][C:8]1([CH3:13])[CH2:9][CH2:10][CH2:11][N:5]([C:3](=[O:4])[CH2:2][N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)[C:6]2[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:7]1=2

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 31268PyrrolidineHCID 67264032HCID 67264032, compound

Product 1

HCID 67264680HCID 67264680, compound

Procedure

2-Chloro-1-(5,5-dimethyl-8-nitro-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl)-ethanone (0.494 g, 0.00166 mol), pyrrolidine (0.310 mL, 0.00371 mol) and N,N-dimethylformamide (5.0 mL, 0.064 mol) were combined in a round bottom flask and stirred at room temperature for 18 hours. The reaction was concentrated under reduced pressure. The residue was dissolved in methylene chloride and washed with water and then brine. The organic phase was dried with magnesium sulfate, filtered and concentrated under reduced pressure. The residue was triturated with ether to yield a crude orange solid, 1-(5,5-Dimethyl-8-nitro-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl)-2-pyrrolidin-1-yl-ethanone. LCMS: m/z=332.33 (M+H+).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in methylene chloride
  3. washwashed with water
  4. dry with materialThe organic phase was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-8912789c1ae04ada88e78be304252e8b
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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