Hydrochloric Acid → HCID 21442579, compound
Reaction equation
[CH:1]([NH:3][C:4]([CH3:20])([CH3:19])[C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)=O.COCCO[AlH2-]OCCOC.[Na+].O.[ClH:34]>C1C=CC=CC=1.CCOCC>[ClH:34].[CH3:1][NH:3][C:4]([CH3:20])([CH3:19])[C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][CH:6]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 2.92 grams of N-formyl-α,α-dimethyl-4-(phenylethynyl)-benzylamine in 30 ml. of benzene is placed in a dry flask. The solution is stirred. A solution of 6.6 grams of a 70% "Red-Al" solution in benzene is diluted with 30 ml. of benzene; this solution is added dropwise over approximately 30 minutes to the solution of N-formyl-α,α-dimethyl-4-(phenylethynyl)-benzylamine. The reaction is hydrolyzed with water and is extracted thoroughly with a 1:1 benzene-ether solvent mixture. The combined extracts are dried over magnesium sulfate, filtered, and the solvent is evaporated to give 3.34 gm. of an oil. This oil is dissolved in ether and treated with ethanolic hydrogen chloride. The precipitate is collected and recrystallized from isopropanol to give N,α,α-trimethyl-4-(phenylethynyl)-benzylamine hydrochloride, m.p. 266°-268° C.
Workup
- extractionis extracted thoroughly with a 1:1 benzene-ether solvent mixture
- dry with materialThe combined extracts are dried over magnesium sulfate
- filtrationfiltered
- customthe solvent is evaporated
- customto give 3.34 gm
- customThe precipitate is collected
- customrecrystallized from isopropanol
Sources & evidence
- ORD record
- ord-a23fd7f97e94430ba98bdea10f7cc8f2
- Source dataset
- uspto-grants-1976_05
- Patent number
- US03957871
Reaction notes
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