2-Bromoethanol → HCID 12527883, compound

HRID 1577010Notes

Reaction equation

HRID 1577010 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][CH:6]3[CH2:11][CH2:12][NH:13][CH2:14][CH:5]3[C:4]=2[CH:3]=1.[CH2:15](Br)[CH2:16][OH:17].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[OH:17][CH2:16][CH2:15][N:13]1[CH2:12][CH2:11][CH:6]2[NH:7][C:8]3[CH:9]=[CH:10][C:2]([CH3:1])=[CH:3][C:4]=3[CH:5]2[CH2:14]1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 10241582HCID 10241582, compound

Product 1

HCID 12527883HCID 12527883, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 8-methyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole (10.0 g), ethylene bromohydrin (8.0 g) and potassium carbonate (14.6 g) in methyl ethyl ketone (80 ml) is refluxed with stirring for 16 hours. The insoluble materials are filtered off and the filtrate is concentrated under reduced pressure. The resulting residue is dissolved in a dilute hydrochloric acid. The dilute hydrochloric acid layer is separated, washed with benzene, made alkaline with aqueous sodium hydroxide and then extracted with benzene. The benzene layer is dried over anhydrous sodium sulfate and concentrated to give a crude product as an oily substance. The crude product is treated in the same manner as described in Example 1 (1) to give the dihydrochloride of the titled compound (7.8 g), m.p. 182° -185°C (recrystallized from aqueous ethanol).

Workup

  1. temperatureis refluxed
  2. filtrationThe insoluble materials are filtered off
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. dissolutionThe resulting residue is dissolved in a dilute hydrochloric acid
  5. customThe dilute hydrochloric acid layer is separated
  6. washwashed with benzene
  7. extractionextracted with benzene
  8. dry with materialThe benzene layer is dried over anhydrous sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-84ee79e26f5f4b8b8e4d2ecf3ed3b18c
Source dataset
uspto-grants-1976_09
Patent number
US03983239

Reaction notes

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