Ammonium Chloride → HCID 54348907, compound

HRID 26224Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([NH:14][CH:15]1[CH2:21][CH2:20][C:19]2[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=2[C:17](=[O:26])[CH2:16]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl-].[NH4+]>O1CCCC1>[OH:26][CH:17]1[C:18]2[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=2[CH2:20][CH2:21][CH:15]([NH:14][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:16]1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 1.5 g of lithium aluminum hydride in 150 ml of anhydrous tetrahydrofuran was cooled to 0° C. and a solution of 8 g of 7-benzylamino-6,7,8,9-tetrahydro [5H] benzocyclohepten-5-one in 150 ml of tetrahydrofuran was added thereto over 30 minutes at 0° to 5° C. The mixture was stirred for 2 hours at 0° C. and was then poured into an aqueous solution saturated with ammonium chloride. The mixture was filtered and the filtrate was extracted with ethyl acetate. The extract was washed with an aqueous sodium chloride solution, was dried and filtered. The filtrate was evaporated to dryness under reduced pressure at 40° C. to 8.4 g of raw product which was a mixture of the A and B isomers of 5ξ-hydroxy-7-benzylamino-6,7,8,9-tetrahydro [5H] benzocycloheptene which was used as is for the next step.

Workup

filtrationThe mixture was filtered
extractionthe filtrate was extracted with ethyl acetate
washThe extract was washed with an aqueous sodium chloride solution
customwas dried
filtrationfiltered
customThe filtrate was evaporated to dryness under reduced pressure at 40° C. to 8.4 g of raw product which
additiona mixture of the A and B isomers of 5ξ-hydroxy-7-benzylamino-6,7,8,9-tetrahydro [5H] benzocycloheptene which

Sources & evidence

ORD record: ord-00a3b3c2272642268bb5ceb50bd17127
Source dataset: uspto-grants-1979_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04148919

Reaction notes

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