Sodium Hydroxide → 6-(2-(3-Benzylpiperidino)-1-hydroxyethyl)-1,2,3,4-tetrahydroquinolin-2-one
Reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][CH2:11][N:10]([CH2:14][C:15]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[NH:23][C:22](=[O:27])[CH2:21][CH2:20]3)=[O:16])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C2C(=CC=CC=2)CCC1=O.ClCC(Cl)=O.[Al+3].[Cl-].[Cl-].[Cl-].CN(C=O)C.ClCC(C1C=C2C(=CC=1)NC(=O)CC2)=O.C(C1CCCNC1)C1C=CC=CC=1.[BH4-].[Na+].[OH-].[Na+]>C(O)C.CO.ClCCl.C(N(CC)CC)C>[CH2:1]([CH:8]1[CH2:13][CH2:12][CH2:11][N:10]([CH2:14][CH:15]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[NH:23][C:22](=[O:27])[CH2:21][CH2:20]3)[OH:16])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
12
Reactant 7
HCID 14798Sodium Hydroxide
HCID 64796Hydrocarbostyril
HCID 1145513-Benzylpiperidine
HCID 4311764Sodium borohydride
HCID 49617906-(2-Chloroacetyl)-1,2,3,4-tetrahydroquinolin-2-one
HCID 158169131,2,3,4-Tetrahydro-6-(2-(3-benzylpiperidino)-1-oxoethyl)quinolin-2-one
HCID 86751733chloroacetyl chloride AlCl3 DMFProduct 1
Reagents, catalysts & solvents 4
Procedure
A solution of 36.2 g of 1,2,3,4-tetrahydro-6-(2-(3-benzylpiperidino)-1-oxoethyl)quinolin-2-one ("A"; racemate; obtainable by reaction of 1,2,3,4-tetrahydroquinolin-2-one with chloroacetyl chloride/AlCl3 /DMF to give 6-chloroacetyl-1,2,3,4-tetrahydroquinolin-2-one ("B") and subsequent reaction with (racemic) 3-benzylpiperidine in ethanol in the presence of triethylamine) in 725 ml of methanol is treated with 3.8 g of NaBH4 and then stirred at 10° for 2 hours. Customary working up (sodium hydroxide solution/dichloromethane) gives 6-(2-(3-benzylpiperidino)-1-hydroxyethyl)-1,2,3,4-tetrahydroquinolin-2-one, racemate ("C").
Workup
- customto give
Sources & evidence
- ORD record
- ord-ce163e3bd5a04c10b181e8d87c272240
- Source dataset
- uspto-grants-1997_12
- Patent number
- US05698553
Reaction notes
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