Hydrochloric Acid → 8-[4-(2-Propoxyethoxy)phenyl]-1-propyl-1,2,3,4-tetrahydro-1-benzazocine-5-carboxylic acid

HRID 1810805Notes

Reaction equation

[CH2:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][C:17]3[N:24]([CH2:25][CH2:26][CH3:27])[CH2:23][CH2:22][CH2:21][C:20]([C:28]([O:30]C)=[O:29])=[CH:19][C:18]=3[CH:32]=2)=[CH:10][CH:9]=1)[CH2:2][CH3:3].[OH-].[Na+].Cl>C(O)C.C1COCC1>[CH2:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][C:17]3[N:24]([CH2:25][CH2:26][CH3:27])[CH2:23][CH2:22][CH2:21][C:20]([C:28]([OH:30])=[O:29])=[CH:19][C:18]=3[CH:32]=2)=[CH:10][CH:9]=1)[CH2:2][CH3:3]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of methyl 8-[4-(2-propoxyethoxy)phenyl]-1-propyl-1,2,3,4-tetrahydro-1-benzazocine-5-carboxylate (1.10 g) in a mixture of ethanol-THF (20-10 ml) was added an aqueous 1N sodium hydroxide solution (5.0 ml) at room temperature. The mixture was stirred at 60° C. for 16 hours and cooled to 0° C. 1N Hydrochloric acid (6 ml) was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried with magnesium sulfate. After concentration under reduced pressure, the precipitated crystals were collected by filtration. The crystals were washed with diisopropylether to give 8-[4-(2-propoxyethoxy)phenyl]-1-propyl-1,2,3,4-tetrahydro-1-benzazocine-5-carboxylic acid (0.80 g) as yellow crystals.

Workup

temperaturecooled to 0° C
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried with magnesium sulfate
concentrationAfter concentration under reduced pressure
filtrationthe precipitated crystals were collected by filtration
washThe crystals were washed with diisopropylether

Sources & evidence

ORD record: ord-c2faa95d92314d0a8822ef9e4d69eba6
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362058B2

Reaction notes

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