Methanol → HCID 19090108, compound

HRID 1463306Notes

Reaction equation

HRID 1463306 reaction equation
[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[C:14](=[O:16])[CH:13]([CH2:17][CH2:18][CH:19]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:21][CH2:20]1)[CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.CO.[BH4-].[Na+]>O>[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[CH:14]([OH:16])[CH:13]([CH2:17][CH2:18][CH:19]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH2:21][CH2:20]1)[CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 19090064HCID 19090064, compound

Product 1

HCID 19090108HCID 19090108, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.41 gm of 9-amino-2-(2-(1-benzylpiperidin-4-yl)ethyl)-1,2,3,4-tetrahydroacridin-1-one was dissolved into 10 ml of methanol. To the solution was added 0.15 gm of sodium borohydride, and the mixture was stirred for 2 hours at room temperature. After the addition of 30 ml of water, the reaction mixture was extracted with chloroform. The extract was washed with saturated brine, dried, and evaporated under reduced pressure. 0.28 gm of 9-amino-2-(2-(1-benzylpiperidin-4-yl)ethyl)-1,2,3,4-tetrahydroacridin-1-ol (Compound (I) with R1 =R3 =H, R2 =--NH2, A=>CH(CH2)n --, Y=>CHOH, m=2 and n=2) was obtained by recrystallizing the residue from ethyl acetate.

Workup

  1. extractionthe reaction mixture was extracted with chloroform
  2. washThe extract was washed with saturated brine
  3. customdried
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b77c1136a12547aca421af44f1960e3b
Source dataset
uspto-grants-1994_04
Patent number
US05300517

Reaction notes

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