Dimethylformamide → HCID 67264680, compound

HRID 1041586Notes

Reaction equation

HRID 1041586 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-7d87361c041b409d86c8cd1ec6aacf2d
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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