Sodium Hydroxide → 9-Chloro-3-methyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole

HRID 1045521Notes

Reaction equation

HRID 1045521 reaction equation
Cl.[CH3:2][N:3]1[CH2:9][CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.Cl.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19]N)=[CH:15][CH:14]=1.[OH-].[Na+]>S(=O)(=O)(O)O.O1CCOCC1>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]2[NH:19][C:6]3[CH2:5][CH2:4][N:3]([CH3:2])[CH2:9][CH2:8][C:7]=3[C:15]=2[CH:14]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 101978461-methylazepan-4-one Hydrochloride

Product 1

HCID 685585079-Chloro-3-methyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared by following general procedure 1. 1-Methylazepan-4-one hydrochloride (164 mg, 1 mmol) and 4-chlorophenylhydrazine hydrochloride (179 mg, 1 mmol) were heated in a mixture of 7% sulfuric acid in 1,4-dioxane (2-3 mL) overnight under nitrogen. Two liquid layers persisted throughout the reaction. The mixture was poured on to ice and basified with 50% aq NaOH. The resulting precipitate was filtered, washed well with water, and dried in air to give 9-chloro-1,2,3,4,5,6-hexahydro-3-methylazepino[4,5-b]indole as a dark brown solid (183 mg 78% yield).

Workup

  1. customThe title compound was prepared
  2. customTwo liquid layers persisted throughout the reaction
  3. additionThe mixture was poured on to ice
  4. filtrationThe resulting precipitate was filtered
  5. washwashed well with water
  6. customdried in air

Sources & evidence

ORD record
ord-b22d70bb0d77442fbabf38a7f17a019c
Source dataset
uspto-grants-2013_10
Patent number
US08569287B2

Reaction notes

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