Benzaldehyde → HCID 20041368, compound

HRID 1762482Notes

Reaction equation

HRID 1762482 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][CH2:10][CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:21]#[N:22])[CH:19]=2)[NH:14][CH:13]=1.[BH4-].[Na+]>C(O)C>[C:2]1([CH2:1][NH:9][CH2:10][CH2:11][C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:21]#[N:22])[CH:19]=3)[NH:14][CH:13]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 589265-CyanotryptamineHCID 4311764Sodium borohydride

Product 1

HCID 20041368HCID 20041368, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Freshly distilled benzaldehyde (2.96 g) was added to a solution of 3-(2-aminoethyl)-1H-indole-5-carbonitrile (5 g) in absolute ethanol (120 ml). The mixture was heated at reflux for 2 h before cooling to 10°. Sodium borohydride (1 g) was added and the suspension stirred for 2 h. The mixture was reduced to dryness and the residue recrystallised from a mixture of toluene and petroleum ether (b.p. 60°-80°). The solid was washed well with water and dried to give the title compound as a powder (3.8 g), m.p 99°-101°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. temperaturebefore cooling to 10°
  4. customthe residue recrystallised from a mixture of toluene and petroleum ether (b.p. 60°-80°)
  5. washThe solid was washed well with water
  6. customdried

Sources & evidence

ORD record
ord-4421b81fe0ac46beb4d752b49596856b
Source dataset
uspto-grants-1989_05
Patent number
US04833153

Reaction notes

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