Reaction #1328413

ord-70be78ee663c4cd4b844a0da586c2e57

Reaction equation

CCN(CC)C(=O)CCl
N,N-diethylchloroacetamide
O
water
C[C@H](Cc1c[nH]c2c(O)cccc12)N1C(=O)c2ccccc2C1=O
(R)-7-hydroxy-3-(2-phthalimidopropyl)indole
O=C([O-])[O-].[K+].[K+]
potassium carbonate
→
CCN(CC)C(=O)COc1cccc2c(C[C@@H](C)N3C(=O)c4ccccc4C3=O)c[nH]c12
title compound
CCN(CC)C(=O)COc1cccc2c(C[C@@H](C)N3C(=O)c4ccccc4C3=O)c[nH]c12
(R)-7-diethylaminocarbonylmethoxy-3-(2-phthalimidopropyl)indole

Reactants

CCN(CC)C(=O)CCl
N,N-diethylchloroacetamide
O
water
C[C@H](Cc1c[nH]c2c(O)cccc12)N1C(=O)c2ccccc2C1=O
(R)-7-hydroxy-3-(2-phthalimidopropyl)indole
—
residue
O=C([O-])[O-].[K+].[K+]
potassium carbonate

Reagents

None

Solvents

CC(C)=O
acetone

Conditions

Temperature
80°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturethe solution was heated
  2. 2
    workup.ADDITIONwas added
  3. 3
    Filtrationa deposited crystal was collected by filtration
  4. 4
    Washwashed with water

Procedure

A residue 10.27 g containing (R)-7-hydroxy-3-(2-phthalimidopropyl)indole was dissolved in 200 ml of acetone, and 8.00 g of potassium carbonate was added thereto. After addition of N,N-diethylchloroacetamide 15.5 ml, the solution was heated to reflux in an oil bath of 80° C. For 3 hours. After cooling down 200 ml of water was added, and a deposited crystal was collected by filtration and washed with water, whereby 9.56 g of the title compound was obtained in the form of a pale yellowish white substance.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07115412B2uspto-grants-2006_10