HCID 15612343, compound → (+/-)-alpha-amino-alpha-methyl-N-(2-phenylethyl)-1H-indole-3-propanamide

HRID 54841Notes

Reaction equation

HRID 54841 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([NH:24]C(=O)OCC2C3C=CC=CC=3C3C2=CC=CC=3)([CH3:23])[C:12](=[O:22])[NH:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:2]1>N1CCCCC1.CN(C=O)C>[NH2:24][C:11]([CH3:23])([CH2:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)[C:12]([NH:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:22]

Participants

4

Reactant 1

HCID 15612343HCID 15612343, compound

Product 1

HCID 14560809(+/-)-alpha-amino-alpha-methyl-N-(2-phenylethyl)-1H-indole-3-propanamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8082PiperidineSolvent

Procedure

(±)-9H-Fluoren-9-ylmethyl [1-(1H-indol-3-ylmethyl)-1-methyl-2-oxo-2-[(2-phenylethyl)amino]ethyl]carbamate (10 g, 18.4 mmol) was dissolved in a 20% piperidine in DMF solution (50 mL) and stirred for 12 hours at room temperature. The solvent was removed in vacuo and chromatographed over silica gel using CH2Cl2 then 5% MeOH:95% CH2Cl2 as eluants. The title compound was crystallized from ethyl acetate (4.73 g, 80%), mp 106°-110° C. (EtOAc); IR (film) 1646 cm-1 ; NMR (CDCl3) δ1.39 (3H, s), 2.56-2.74 (2H, m), 2.82 (1H, d, J 14Hz), 3.28-3.40 (1H, m), 3.48 (1H, d, J 14Hz), 3.44-3.53 (1H, m), 7.1-7.7 (11H, m), 8.3 (1H, s); Anal. (C20H23N3O) C, H, N.

Workup

  1. customThe solvent was removed in vacuo
  2. customchromatographed over silica gel
  3. customThe title compound was crystallized from ethyl acetate (4.73 g, 80%), mp 106°-110° C. (EtOAc)

Sources & evidence

ORD record
ord-71ab1fce44f14448ae074500a0994878
Source dataset
uspto-grants-1997_04
Patent number
US05622983

Reaction notes

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