2-Chloro-N,N-dimethylethylamine → HCID 20545917, compound

HRID 2059324Notes

Reaction equation

HRID 2059324 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[C:13](=[CH:14][C:15]([OH:19])=[CH:16][CH:17]=3)[C:12](=[O:20])[C:11]([CH3:22])([CH3:21])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[H-].[Na+].[H][H].[CH3:27][N:28]([CH3:32])[CH2:29][CH2:30]Cl>C1(C)C=CC=CC=1>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH2:30][CH2:29][N:28]([CH3:32])[CH3:27])=[CH:16][CH:17]=3)[C:12](=[O:20])[C:11]([CH3:22])([CH3:21])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 20545912HCID 20545912, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20545917HCID 20545917, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 4-(3,4-dichlorophenyl)-7-hydroxy-2,2-dimethyl-1-tetralone (2.3 g) and sodium hydride (0.4 g, 60% dispersion in oil) was refluxed in toluene (20 ml) until evolution of hydrogen had ceased. A solution of 2-dimethylaminoethylchloride (1.2 g) in toluene (15 ml) was added dropwise and the mixture refluxed for 3 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 the product as the free base, which was converted to the hydrochloride salt. Recrystallisation from ether-ethyl acetate gave 4-(3,4-dichlorophenyl)-2,2-dimethyl-7-(2-dimethylaminoethoxy)-1-tetralone hydrochloride as white crystals, (2.2 g, 72%) m.p. 180°-5° C.

Workup

  1. temperaturethe mixture refluxed for 3 hr
  2. customThe solvent was removed
  3. customThe aqueous layer was separated
  4. extractionextracted with ether
  5. dry with materialthe extract dried (MgSO4)
  6. customEvaporation
  7. customgave the product as the free base, which
  8. customRecrystallisation from ether-ethyl acetate

Sources & evidence

ORD record
ord-d7d71f654b87484cbf2817133df0e0d1
Source dataset
uspto-grants-1982_03
Patent number
US04322370

Reaction notes

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