Sodium borohydride → HCID 19029921, compound

HRID 2256396Notes

Reaction equation

HRID 2256396 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]3[C:23](=[O:24])[C:22]4=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]4[C:20]3=[O:29])[CH:12]=2)[NH:7][CH:6]=1.[BH4-].[Na+]>CO>[NH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]3[CH:23]([OH:24])[C:22]4[C:21](=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:20]3=[O:29])[CH:12]=2)[NH:7][CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19029941HCID 19029941, compound

Product 1

HCID 19029921HCID 19029921, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(2-aminoethyl)-5-(4-phthalimidobutyloxy)-1H-indole hydrochloride (0.057 g, 0.14 mmol) in methanol (10 mL) was added sodium borohydride (0.057 g, 1.36 mmol) and the resulting mixture was stirred at room temperature for 4 hours. The solution was then poured onto a silica gel column and the product eluted with methanol/ammonium hydroxide (19:1) to give the title compound as a syrup (0.052 g, 100%).

Workup

  1. additionThe solution was then poured onto a silica gel column
  2. washthe product eluted with methanol/ammonium hydroxide (19:1)

Sources & evidence

ORD record
ord-40066e57761f42a08f1a3a48550e55e8
Source dataset
uspto-grants-1997_08
Patent number
US05654431

Reaction notes

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