Potassium Carbonate → HCID 13592682, compound

HRID 1193495Notes

Reaction equation

HRID 1193495 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH2:9][CH2:8]2)=[O:4].[CH3:16][C:17]([CH3:29])([NH2:28])[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][CH3:27].C(=O)([O-])[O-].[K+].[K+].[BH4-].[Na+]>CN(C)C=O.CO>[OH:4][CH:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH2:9][CH2:8]2)[CH2:2][NH:28][C:17]([CH3:29])([CH3:16])[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][CH3:27]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 27568376-(Bromoacetyl)-3,4-dihydroquinolin-2(1H)-oneHCID 4311764Sodium borohydrideHCID 183496784-(2-Methoxyphenyl)-2-methylbutan-2-amine

Product 1

HCID 13592682HCID 13592682, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

6.0 g (0.023 mole) of 3,4-dihydro-6-bromoacetylquinolin-2(1H)-one, 4.8 g (0.025 mole) of 1,1-dimethyl-3-(2-methoxy-phenyl)-propanamine and 3.2 g (0.03 mole) of potassium carbonate are stirred in 100 ml of dimethylformamide at room temperature for 24 hours. After dilution with methanol, the product is reduced with an excess of sodium borohydride. The solvents are removed in vacuo, the residue is taken up in methylene chloride and the mixture is extracted with water. Column chromatography on silica gel (CHCl3 /MeOH 90/10) gives 3,4-dihydro-6-[1-hydroxy-2-[[1,1-dimethyl-3-(2-methoxy-phenyl)-propyl]-amino]-ethyl]-quinolin-2(1H)-one as a base, which is converted into the hydrochloride in the customary manner. Melting point 180° C. (decomposition).

Workup

  1. customThe solvents are removed in vacuo
  2. extractionthe mixture is extracted with water

Sources & evidence

ORD record
ord-705892703e92446b956e028de11cbadf
Source dataset
uspto-grants-1989_03
Patent number
US04810712

Reaction notes

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