Water → 2-{[5-(4-Chlorophenyl)-7,7-dimethyl-8-methylidene-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}-N,N-dimethylethan-1-amine

HRID 2059314Notes

Reaction equation

HRID 2059314 reaction equation
[CH3:1][Li].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[C:19]3[C:14](=[CH:15][C:16]([O:20][CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])=[CH:17][CH:18]=3)[C:13](=O)[C:12]([CH3:28])([CH3:27])[CH2:11]2)=[CH:6][CH:5]=1.O>CCOCC>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[C:19]3[C:14](=[CH:15][C:16]([O:20][CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])=[CH:17][CH:18]=3)[C:13](=[CH2:1])[C:12]([CH3:28])([CH3:27])[CH2:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 20545909HCID 20545909, compoundHCID 178418348HCID 178418348, compound2×

Product 1

HCID 30258092-{[5-(4-Chlorophenyl)-7,7-dimethyl-8-methylidene-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}-N,N-dimethylethan-1-amine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

An ethereal solution of methyllithium (50 ml, 1.9 M) was added over 45 min. to a stirred solution of 4-(4-chlorophenyl)-2,2-dimethyl-7-(2-dimethylaminoethoxy)-1-tetralone (18.5 g) in dry ether (150 ml) and the mixture heated under reflux for 30 min. After cooling, excess methyllithium was decomposed with water, the ether layer was separated, dried (MgSO4) and treated with a solution of hydrogen chloride in ether. The hydrochloride salt of 4-(4-chlorophenyl)-2,2-dimethyl-7-(2-dimethylaminoethoxy)-1-methylidene tetralin precipitated as a white solid (15.6 g, 77%). A portion was recrystallized from ethanol-ether, m.p. 233°-235°.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 30 min
  3. temperatureAfter cooling
  4. customthe ether layer was separated
  5. dry with materialdried (MgSO4)
  6. additiontreated with a solution of hydrogen chloride in ether
  7. customThe hydrochloride salt of 4-(4-chlorophenyl)-2,2-dimethyl-7-(2-dimethylaminoethoxy)-1-methylidene tetralin precipitated as a white solid (15.6 g, 77%)
  8. customA portion was recrystallized from ethanol-ether, m.p. 233°-235°

Sources & evidence

ORD record
ord-b2cbbcf331624395b47091a73a0f2d57
Source dataset
uspto-grants-1982_03
Patent number
US04322370

Reaction notes

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