2-Chloro-N,N-dimethylethylamine → HCID 20545909, compound

HRID 2059311Notes

Reaction equation

HRID 2059311 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]3[C:12](=[CH:13][C:14]([OH:18])=[CH:15][CH:16]=3)[C:11](=[O:19])[C:10]([CH3:21])([CH3:20])[CH2:9]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:24][N:25]([CH3:29])[CH2:26][CH2:27]Cl>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]3[C:12](=[CH:13][C:14]([O:18][CH2:27][CH2:26][N:25]([CH3:29])[CH3:24])=[CH:15][CH:16]=3)[C:11](=[O:19])[C:10]([CH3:21])([CH3:20])[CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 20545898HCID 20545898, compound

Product 1

HCID 20545909HCID 20545909, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-(4-chlorophenyl)-7-hydroxy-2,2-dimethyl-1-tetralone (14.7 g), sodium hydride (80% oil dispersion, 1.65 g) and 2-dimethylaminoethyl chloride (5.8 g) was heated under reflux in toluene (150 ml) for 6 hr. The solvent was removed and the residue shaken with ether-dilute hydrochloric acid. The aqueous layer was separated, basified, extracted with ether and the extract dried (MgSO4). Evaporation gave 4-(4-chlorophenyl)-2,2-dimethyl-7-(2-dimethylaminoethoxy)-1-tetralone as a yellow oil (17 g, 91%) which was contaminated with ether. A portion was converted to the hydrochloride salt (64%), which crystallised as white prisms from ethanol-ether, m.p. 209°-211°.

Workup

  1. temperaturewas heated
  2. customThe solvent was removed
  3. customThe aqueous layer was separated
  4. extractionextracted with ether
  5. dry with materialthe extract dried (MgSO4)
  6. customEvaporation

Sources & evidence

ORD record
ord-6a3fd53d1704454083045916ec36ad91
Source dataset
uspto-grants-1982_03
Patent number
US04322370

Reaction notes

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