Sodium Hydroxide → HCID 135752, compound

HRID 1156551Notes

Reaction equation

[I-].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:10]23[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]2[N+:13]([CH3:20])([CH3:19])[CH2:12][CH2:11]3)[CH:7]=[CH:8][CH:9]=1.[OH-].[Na+]>O>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:10]2([CH2:11][CH2:12][N:13]([CH3:20])[CH3:19])[CH2:18][CH2:17][CH2:16][CH:15]=[CH:14]2)[CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 170 °C

Procedure

1 g of hexahydro-3a-(m-methoxyphenyl)-1,1-dimethyl-indolinium iodide is dissolved in 40 ml of water. The solution is applied to a column containing 50 g of Amberlite IRA 400 (pre-treated with sodium hydroxide; washed with distilled water until neutral). Thereafter, the column is eluted with 500 ml of distilled water. After distillation of the water, the hexahydro-3a-(m-methoxyphenyl)-1,1-dimethyl-indolinium hydroxide remaining as the residue is heated at 170° C. in a distillation apparatus in a high vacuum, an oil distilling over. This oil still contains, besides rac. 1-(m-methoxyphenyl)-N,N-dimethyl-2-cyclohexene-1-ethylamine, a relatively small amount of hexahydro-3a-(m-methoxyphenyl)-1-methylindoline.

Workup

additioncontaining
washThereafter, the column is eluted with 500 ml of distilled water
distillationAfter distillation of the water
distillationan oil distilling over

Sources & evidence

ORD record: ord-3451f4011ef54887bec9423424974797
Source dataset: uspto-grants-1982_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04336268

Reaction notes

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