Water → (R)-7-diethylaminocarbonylmethoxy-3-(2-phthalimidopropyl)indole

HRID 1241231Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH2:11][C@H:12]([N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24])[CH3:13].C(=O)([O-])[O-].[K+].[K+].[CH2:31]([N:33]([CH2:38][CH3:39])[C:34](=[O:37])[CH2:35]Cl)[CH3:32].O>CC(C)=O>[CH2:31]([N:33]([CH2:38][CH3:39])[C:34]([CH2:35][O:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH2:11][C@H:12]([N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24])[CH3:13])=[O:37])[CH3:32]

Participants

Conditions

Temperature: 80 °C

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.

Workup

temperaturethe solution was heated
additionwas added
filtrationa deposited crystal was collected by filtration
washwashed with water

Sources & evidence

ORD record: ord-70be78ee663c4cd4b844a0da586c2e57
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115412B2

Reaction notes

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