Acetaldehyde → 5-Diethylaminomethyl-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester

HRID 966536Notes

Reaction equation

HRID 966536 reaction equation
Cl.[CH2:2]([O:9][C:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:21][NH2:22])[CH:19]=2)[NH:14][C:13]=1[CH3:23])=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:24](=O)[CH3:25].[C:27](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:28].[Na+]>ClC(Cl)C>[CH2:2]([O:9][C:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:21][N:22]([CH2:24][CH3:25])[CH2:27][CH3:28])[CH:19]=2)[NH:14][C:13]=1[CH3:23])=[O:11])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 1317251805-Aminomethyl-2-methyl-1h-indole-3-carboxylic acid benzyl ester, hydrochloride

Product 1

HCID 99682915-Diethylaminomethyl-2-methyl-1H-indole-3-carboxylic Acid Benzyl EsterYield 34%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a mixture of 5-aminomethyl-2-methyl-1H-indole-3-carboxylic acid benzyl ester, hydrochloride (300 mg, 0.91 mmol, Example 63, Step E) and in dichloroethane (40 mL) was added acetaldehyde (0.1 mL, 1.82 mmol). The mixture was stirred for 0.5 hour and then sodium triacetoxyborohydride (289 mg, 1.37 mmol) was added. The mixture was stirred at room temperature overnight and then partitioned between methylene chloride and water. The organic phase was washed with saturated sodium bicarbonate solution and brine, dried over Na2SO4, and filtered. The filtrate was concentrated in vacuo to give a solid residue, which was purified by chromatography (5%-15% methanol in methylene chloride) to give 107 mg (34%) of the desired product as a white solid: mp 106-108° C.; MS(APCI+): m/z 351.1 (MH+); Anal. Calcd for C22H26N2O2.0.25H2O: C, 74.44; H, 7.52; N, 7.89. Found: C, 74.30; H, 7.51; N, 7.79.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. custompartitioned between methylene chloride and water
  3. washThe organic phase was washed with saturated sodium bicarbonate solution and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customto give a solid residue, which
  8. customwas purified by chromatography (5%-15% methanol in methylene chloride)

Sources & evidence

ORD record
ord-a300d01a1c3345df9889101bae67ff50
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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