Water → HCID 12813968, compound

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:21]=[CH:20][C:19]2[N:18]([CH3:22])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:28](OC)=[O:29])([CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[C:10]=2[CH:9]=1.O>O1CCCC1>[Cl:7][C:8]1[CH:21]=[CH:20][C:19]2[N:18]([CH3:22])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([CH2:28][OH:29])([CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[C:10]=2[CH:9]=1

Participants

Procedure

14 cc of tetrahydrofuran were cooled to 0°C and 0.9 gm of lithium aluminum hydride and then a solution of 1.4 gm of 2-chloro-9-methoxycarbonyl-9-(β-dimethylaminoethyl)-10-methyl-acridane in 14 cc of tetrahydrofuran were added thereto while maintaining the temperature below +10°C. The reaction mixture was then heated at reflux for 21/2 hours and cooled to 0°, +5°C and 10 cc of tetrahydrofuran containing 20% water and then 50 cc of water were added thereto. The reaction mixture was extracted with methylene chloride and filtered. The organic phases were washed with an aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated to dryness to obtain 1.15 gm of 2-chloro-9-hydroxymethyl-9-(β-dimethylaminoethyl)-10-methyl-acridane which was used as is for the next step.