4-(2-Chloroethyl)morpholine → 5-[2-(Morpholin-4-yl)ethyl]thiopyrano[3,2-b]indol-4(5H)-one

HRID 437789Notes

Reaction equation

HRID 437789 reaction equation
[S:1]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[NH:6][C:5]=2[C:4](=[O:14])[CH:3]=[CH:2]1.Cl[CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>>[O:21]1[CH2:22][CH2:23][N:18]([CH2:17][CH2:16][N:6]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]3[S:1][CH:2]=[CH:3][C:4](=[O:14])[C:5]2=3)[CH2:19][CH2:20]1

Participants

3

Reactant 2

HCID 767274-(2-Chloroethyl)morpholineHCID 20326608Thiopyrano[3,2-b]indol-4(5H)-one

Product 1

HCID 203266215-[2-(Morpholin-4-yl)ethyl]thiopyrano[3,2-b]indol-4(5H)-oneYield 68%

Procedure

4.8 g of thiopyrano [3,2-b]indol-4(5H)-one and 15 g of chloroethylmorpholine, are reacted in the same manner as described in Example 14, except that the crude free base crystallized. This is filtered and recrystallized from methylenechloride-hexane to give 5.1 g of product, mp 136°-137° C.

Workup

  1. customexcept that the crude free base crystallized
  2. filtrationThis is filtered
  3. customrecrystallized from methylenechloride-hexane

Sources & evidence

ORD record
ord-2323bfea0c7547a08d306360319ef25e
Source dataset
uspto-grants-1977_06
Patent number
US04032537

Reaction notes

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