Sodium Hydroxide → HCID 59368456, compound

HRID 1481410Notes

Reaction equation

HRID 1481410 reaction equation
CN1CCC2C3C=C(C)C=CC=3NC=2CC1.[Cl:17][C:18]1[CH:41]=[CH:40][C:21]([CH2:22][CH2:23][N:24]2[C:32]3[CH:31]=[CH:30][C:29]([CH3:33])=[CH:28][C:27]=3[C:26]3[CH2:34][CH2:35][N:36]([CH3:39])[CH2:37][CH2:38][C:25]2=3)=[CH:20][CH:19]=1.[OH-].[Na+].BrCCC1C=CC(Cl)=CC=1>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:22][CH2:23][N:24]2[C:32]3[CH:31]=[CH:30][C:29]([CH3:33])=[CH:28][C:27]=3[C:26]3[CH2:34][CH2:35][N:36]([CH3:39])[CH2:37][CH2:38][C:25]2=3)=[CH:40][CH:41]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 230291-(2-Bromoethyl)-4-chlorobenzeneHCID 86642473HCID 86642473, compound

Product 1

HCID 59368456HCID 59368456, compound

Reagents, catalysts & solvents 1

HCID 70681Tetrabutylammonium ChlorideCatalyst

Procedure

The title compound was prepared by following general procedure 4. 6-(4-Chlorophenethyl)-3,9-dimethyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole 3,9-dimethyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (0.214 g, 1 mmol) along with tetrabutylammonium chloride (0.138 g, 0.0005 mmol) were taken into 50% aq. NaOH solution (5 mL) and stirred for 5 min. at RT, 1-(2-bromoethyl)-4-chlorobenzene (0.219 g, 1 mmol) was added and stirred for 5 min. at RT and then the reaction mixture was heated at 110° C. for overnight. The product detected by LCMS, extracted in ethyl acetate, dried over anhydrous sodium sulfate, concentrated and purified by reverse phase chromatography to get the pure compound 6-(4-chlorophenethyl)-3,9-dimethyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole.

Workup

  1. customThe title compound was prepared
  2. stirringstirred for 5 min. at RT
  3. temperaturethe reaction mixture was heated at 110° C. for overnight
  4. extractionextracted in ethyl acetate
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. custompurified by reverse phase chromatography

Sources & evidence

ORD record
ord-0fe98ac71b4443b49648cf64e6fa1fda
Source dataset
uspto-grants-2016_08
Patent number
US09409910B2

Reaction notes

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