Water → HCID 59807097, compound

HRID 1922395Notes

Reaction equation

HRID 1922395 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]2[NH:8][C:9](=[O:13])[CH2:10][CH2:11][CH2:12][C:6]=2[CH:5]=1)([O-:3])=[O:2].Cl.Cl[CH2:18][CH2:19][N:20]([CH3:22])[CH3:21].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.CO.C(Cl)Cl>[CH3:21][N:20]([CH3:22])[CH2:19][CH2:18][N:8]1[C:9](=[O:13])[CH2:10][CH2:11][CH2:12][C:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:15]=[CH:14][C:7]1=2

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium Carbonate2×HCID 3561757-nitro-2,3,4,5-tetrahydro-1H-1-benzazepin-2-oneHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride2×

Product 1

HCID 59807097HCID 59807097, compoundYield 62.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 21226129Dichloromethane methanolSolvent

Procedure

A suspension of 7-nitro-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one (490 mg, 2.38 mmol), 2-chloro-N,N-dimethylethanamine hydrochloride (685 mg, 4.75 mmol) and potassium carbonate (1.97 g, 14.28 mmol) in 15 mL DMF was stirred at room temperature for 1 day. A TLC analysis indicated that the starting material was still present. The mixture was treated with 2-chloro-N,N-dimethylethanamine hydrochloride (685 mg, 4.75 mmol) and potassium carbonate (1.97 g, 14.28 mmol) followed by 5 mL DMF and stirring was continued at room temperature for 18 hours. After this time, the mixture was poured into 50 mL H2O, then extracted with 2×100 mL EtOAc. The combined organic fractions were washed with brine, dried over Na2SO4, filtered, and concentrated to give a dark residue. The residue was subjected to flash chromatography on silica gel using 2-5% 2M NH3 in MeOH/CH2Cl2 to give a yellow viscous oil (412 mg, 62.4%). 1H-NMR (DMSO-d6) δ 8.21-8.15 (m, 2H), 7.67 (d, J=8.7 Hz, 1H), 3.92-3.90 (m, 2H), 2.87-2.83 (m, 2H), 2.27 (t, J=6.3 Hz, 2H), 2.21-2.11 (m, 4H), 2.03 (s, 6H). MS (EI): 278.1 (M+1).

Workup

  1. stirringstirring
  2. waitwas continued at room temperature for 18 hours
  3. extractionextracted with 2×100 mL EtOAc
  4. washThe combined organic fractions were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a dark residue

Sources & evidence

ORD record
ord-f36f847bd6ab49a7986065169dcf329f
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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