Sodium borohydride → Indoramin

HRID 971955Notes

Reaction equation

HRID 971955 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)(CC)C.CO>[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 33625Indoramin

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6568(+-)-2-ButanolSolvent

Procedure

A suspension of 4-benzamido-1-[2-(3-indolyl)ethyl]-pyridinium bromide (10.5g) and sodium borohydride (2.8 g) in sec-butanol (100 ml) was stirred and refluxed for 6 hours. The reaction mixture was cooled to 25° and diluted with aqueous methanol. The product was separated by filtration and washed with aqueous methanol then with water and finally with methanol, and dried to give the crude title compound. This was purified as described in Example 5 to give the title compound mp 203°-5° C.

Workup

  1. temperaturerefluxed for 6 hours
  2. temperatureThe reaction mixture was cooled to 25°
  3. customThe product was separated by filtration
  4. washwashed with aqueous methanol
  5. dry with materialwith water and finally with methanol, and dried
  6. customto give the crude title compound
  7. customThis was purified

Sources & evidence

ORD record
ord-349f1a04b1194ffbab9ea60b43cd7da3
Source dataset
uspto-grants-1979_07
Patent number
US04162252

Reaction notes

Loading…