Benzaldehyde → HCID 19022968, compound

HRID 1034466Notes

Reaction equation

HRID 1034466 reaction equation
[C:1]([CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH2:16][CH2:17][NH2:18])([O:3][CH2:4][CH3:5])=[O:2].[CH:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[BH4-].[Na+]>CCO>[CH2:19]([NH:18][CH2:17][CH2:16][C:10]1[C:9]2[C:13](=[CH:14][CH:15]=[C:7]([CH2:6][C:1]([O:3][CH2:4][CH3:5])=[O:2])[CH:8]=2)[NH:12][CH:11]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 4311764Sodium borohydrideHCID 11776671HCID 11776671, compound

Product 1

HCID 19022968HCID 19022968, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-[5-carboethoxymethyl-1H-indol-3-yl]ethylamine (2.8 g, 11.37 mmol) in EtOH (45 ml) was added freshly distilled benzaldehyde (1.21 g, 11.37 mmol) and the resulting solution was stirred at room temperature for 22 h. NaBH4 (0.434 g, 11.48 mmol) was added portionwise over 10 min at room temperature and the resulting mixture was stirred for a further 0.5 h before the solvent was removed under vacuum. The resulting residue was taken up into water (20 ml) and acidified with 1N HCl (30 ml). The mixture was then basified with 2N NaOH and extracted with EtOAc (4×70 ml). The combined organic phases were washed with brine (50 ml), dried and concentrated. Chromatography of the residue on silica-gel eluting with CH2Cl2 /EtOH (90:10) gave the title-product (2.78 g, 73%); δ(360 MHz, CDCl3) 1.25 (3H, t, J=7.1 Hz, CH3); 2.98 (4H, s, 2 of CH2); 3.68 (2H, s, CH2); 3.81 (2H, s, CH2); 4.14 (2H, q, J=7.1 Hz, CH2); 6.98 (1H, d, J=2.2 Hz, Ar-H); 7.11 (1H, dd, J=1.6 and 8.3 Hz, Ar-H); 7.20-7.32 (6H, m, Ar-H); 7.49 (1H, d, J=0.7 Hz, Ar-H); 7.99 (1H, br s, indole N-H).

Workup

  1. stirringthe resulting mixture was stirred for a further 0.5 h before the solvent
  2. customwas removed under vacuum
  3. extractionextracted with EtOAc (4×70 ml)
  4. washThe combined organic phases were washed with brine (50 ml)
  5. customdried
  6. concentrationconcentrated
  7. washChromatography of the residue on silica-gel eluting with CH2Cl2 /EtOH (90:10)

Sources & evidence

ORD record
ord-ae49981ae1b544a083df4f6e5cfa23bc
Source dataset
uspto-grants-1994_05
Patent number
US05317103

Reaction notes

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