Sodium Hydroxide → 3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-ylmethyl)benzoic acid

HRID 1034071Notes

Reaction equation

[OH-].[Na+].[CH:3]1[C:13]2[CH2:12][CH2:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[N:8]([CH2:18][C:19]3[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=3)[C:22]([O:24]C)=[O:23])[C:7]=2[CH:6]=[CH:5][CH:4]=1>O1CCOCC1.CO>[CH:14]1[C:10]2[CH2:11][CH2:12][C:13]3[CH:3]=[CH:4][CH:5]=[CH:6][C:7]=3[N:8]([CH2:18][C:19]3[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=3)[C:22]([OH:24])=[O:23])[C:9]=2[CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 25 °C

Procedure

1N aqueous solution of sodium hydroxide (9 ml) was added to a solution of methyl 3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-ylmethyl)benzoate (1.06 g) in a mixture of 1,4-dioxane (25 ml) and methanol (15 ml) at 25° C. The mixture was stirred at 25° C. for 3 hours, and then at 50° C. for 30 minutes. After evaporation of the solvent, the residue was partitioned between ethyl acetate and 0.1N hydrochloric acid. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated to give 3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-ylmethyl)benzoic acid (1.01 g) as powder.

Workup

waitat 50° C. for 30 minutes
customAfter evaporation of the solvent
customthe residue was partitioned between ethyl acetate and 0.1N hydrochloric acid
customThe organic layer was separated
washwashed with water and brine
dry with materialdried over magnesium sulfate
customevaporated

Sources & evidence

ORD record: ord-1eb71c34063a4e00b5abb32653d1c835
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05312829

Reaction notes

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