Sodium borohydride → Indoramin

HRID 971951Notes

Reaction equation

HRID 971951 reaction equation
[Br-].[C:2]([NH:10][C:11]1[CH:16]=[CH:15][N+:14]([CH2:17][CH2:18][C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)=[CH:13][CH:12]=1)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[BH4-].[Na+]>C(O)(C)C.O>[C:2]([NH:10][CH:11]1[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)[CH2:15][CH2:16]1)(=[O:9])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 18177187HCID 18177187, compound

Product 1

HCID 33625IndoraminYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A suspension of 4-benzamido-1-[2-(3-indolyl)ethyl] pyridinium bromide (4.2 g.) and sodium borohydride (1.14 g.) in isopropanol (50 ml.) was refluxed for 31/2 hours. After cooling, the reaction mixture was diluted with water (50 ml.). The product was separated by filtration, washed with water then with acetone and dried to give the title compound in 82% yield, m.p. 203°- 5° C.

Workup

  1. temperaturewas refluxed for 31/2 hours
  2. temperatureAfter cooling
  3. customThe product was separated by filtration
  4. washwashed with water
  5. dry with materialwith acetone and dried

Sources & evidence

ORD record
ord-e168fdbde9b94738b3fb958d5efe1950
Source dataset
uspto-grants-1979_07
Patent number
US04162252

Reaction notes

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