Ammonia → HCID 19598473, compound

HRID 1291935Notes

Reaction equation

HRID 1291935 reaction equation
C([BH3-])#N.[Na+].[OH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][N:10]2[CH2:15][CH:16]([OH:18])[CH3:17].N>C(O)(=O)C>[OH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH2:8][CH2:9][N:10]2[CH2:15][CH:16]([OH:18])[CH3:17]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5003444Sodium cyanoborohydrideHCID 22483528HCID 22483528, compound

Product 1

HCID 19598473HCID 19598473, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.4 g of sodium cyanoborohydride were added to a solution of 7 g of 4-hydroxy-1-N-(β-hydroxypropyl)indole, obtained in the preceding stage, in 40 cm3 of acetic acid, the temperature being maintained below 30° C. After stirring for 30 minutes, the reaction mixture was poured onto 200 g of ice-cold water and the pH was neutralized to 7.5 by addition of 30% aqueous ammonia. The precipitate obtained was filtered off and dried. 4 g of the expected product were obtained, the melting point of which was between 130° and 131° C. and the elemental analysis of which, calculated for C11H15NO2, was as follows:

Workup

  1. temperaturethe temperature being maintained below 30° C
  2. customThe precipitate obtained
  3. filtrationwas filtered off
  4. customdried

Sources & evidence

ORD record
ord-228255cfe1e24e439c8676d4aea5adda
Source dataset
uspto-grants-1998_05
Patent number
US05755829

Reaction notes

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