2-Chloro-N,N-dimethylethylamine → HCID 21446110, compound

HRID 597710Notes

Reaction equation

HRID 597710 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:16]3[C:11]([CH2:12][CH2:13][CH2:14][CH2:15]3)=[CH:10][C:9]2=[O:17])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[CH3:24][N:25]([CH3:29])[CH2:26][CH2:27]Cl>>[CH3:24][N:25]([CH3:29])[CH2:26][CH2:27][O:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:16]3[C:11]([CH2:12][CH2:13][CH2:14][CH2:15]3)=[CH:10][C:9]2=[O:17])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 21446101HCID 21446101, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21446110HCID 21446110, compoundYield 58.3%

Conditions

Temperature
60 °C

Procedure

In accordance with the procedure described in Example 1b), 22.9 g (0.1 mol) of 1-(4-hydroxyphenyl)2-oxo-2,4,5,6,7,7 a-hexahydro-indole were added to a solution of potassium tertiary-butoxide [potassium metal: 3.9 g (1.1 mol); tertiary-butanol, 100 cm3 ], and this solution was added to 11.8 g (0.11 mole) of 2-dimethylamino-1-chloroethane. After heating for 6 hours at 60° C, the crude product of the reaction was isolated as in Example 1b), and purified by crystallisation from hexane. 17.5 g (yield 57%) of 1-[4-(2-dimethylaminoethoxy)-phenyl]-2-oxo-2,4,5,6,7,7a-hexahydro-indole, m.p. 90° C, were obtained.

Workup

  1. customthe crude product of the reaction was isolated as in Example 1b), and
  2. custompurified by crystallisation from hexane

Sources & evidence

ORD record
ord-298e185d245b4f2f9ac1c37805da6a35
Source dataset
uspto-grants-1977_03
Patent number
US04015002

Reaction notes

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