Sodium Hydroxide → HCID 14595976, compound

HRID 1886099Notes

Reaction equation

Cl.[F:2][C:3]([F:31])([F:30])[C:4]1[CH:29]=[CH:28][C:7]([O:8][C@@H:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][C@@H:10]2[CH2:18][N:19]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH3:20])=[CH:6][CH:5]=1.[OH-].[Na+]>>[F:2][C:3]([F:30])([F:31])[C:4]1[CH:29]=[CH:28][C:7]([O:8][C@@H:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][C@@H:10]2[CH2:18][N:19]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH3:20])=[CH:6][CH:5]=1

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 70290830HCID 70290830, compound

Product 1

HCID 14595976HCID 14595976, compound

Procedure

Treat CIS-2,3-dihydro-1-(4-trifluoromethylphenoxy)-N-benzyl-N-methyl-1H-indene-2-methanamine hydrochloride with a sodium hydroxide solution to obtain the oily base CIS-2,3-dihydro-1-(4-trifluoromethylphenoxy)-N-benzyl-N-methyl-1H-indene-2-methanamine. Dissolve CIS-2,3-dihydro-1-(4-trifluoromethylphenoxy)-N-benzyl-N-methyl-1H-indene-2-methanamine (11.9 g, 0.029M) in 150 ml of methylene chloride and to this solution add potassium carbonate (5 g). Add phenylchloroformate (5.4 g, 0.034 M) dropwise and stir the mixture for 3 hours. Sequentially shake the mixture with water, dilute hydrochloric acid and then water. Dry the organic layer over magnesium sulfate. Remove the solvent and recrystallize the residue from cyclohexane to yield 8.9 g (69% yield) of the title compound [melting point=101°-102° C⟧

Sources & evidence

ORD record: ord-658b740ca8ee4791a3e1b24389303f0c
Source dataset: uspto-grants-1992_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05149714

Reaction notes

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