Tetrahydrofuran → HCID 12234597, compound

HRID 1414699Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[CH:12]([N:14]1[C:20]2[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:19]=2[C:18]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:17][CH2:16][CH2:15]1)=O.[Al]>O>[CH3:12][N:14]1[C:20]2[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:19]=2[CH:18]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:17][CH2:16][CH2:15]1

Participants

Conditions

Temperature: 55 °C

Procedure

To a suspension of 400 mg. of lithium aluminum hydride in 10 ml. of tetrahydrofuran is added a solution of 600 mg. of 1-formyl-5-phenyl-7-chloro-2,3-dihydro-1H-1,4-benzodiazepine in 40 ml. of tetrahydrofuran at a room temperature. After the reaction mixture is stirred for one hour at 55° C., water is added thereto carefully. The addition of water is stopped when an aluminum compound begin to precipitate on the bottom of the flask, and the precipitate is removed by filtration. The filtrate is concentrated under a reduced pressure to a solidal substance. The solidal substance is recrystallized from a solvent mixture of benzene and n-hexane to give 400 mg. of 1-methyl-5-phenyl-7-chloro-1,2,4,5-tetrahydro-1H-benzodiazepine, melting point 128°-129° C.

Workup

additionTo a suspension of 400 mg
customat a room temperature
customto precipitate on the bottom of the flask
customthe precipitate is removed by filtration
concentrationThe filtrate is concentrated under a reduced pressure to a solidal substance
customThe solidal substance is recrystallized from a solvent mixture of benzene and n-hexane
customto give 400 mg

Sources & evidence

ORD record: ord-fdd06873aa204b12bb4d9626f5879ff9
Source dataset: uspto-grants-1977_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04002611

Reaction notes

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