Acetone → HCID 21447165, compound

HRID 267965Notes

Reaction equation

HRID 267965 reaction equation
[OH:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]2[C:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]4[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]4)[CH2:11][C:10]=3[C:23](=[O:25])[O:24][C:4]=2[CH:3]=1.[CH2:26](OS(OCC)(=O)=O)[CH3:27].C([O-])([O-])=O.[K+].[K+].[CH3:41][C:42](C)=O>>[CH2:26]([O:1][C:2]1[C:7]([O:8][CH2:41][CH3:42])=[CH:6][C:5]2[C:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]4[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]4)[CH2:11][C:10]=3[C:23](=[O:25])[O:24][C:4]=2[CH:3]=1)[CH3:27]

Participants

5

Reactant 4

HCID 180AcetoneHCID 6163Diethyl SulfateHCID 11430Potassium CarbonateHCID 21447172HCID 21447172, compound

Product 1

HCID 21447165HCID 21447165, compound

Procedure

A mixture of 0.01 m of 1,2,3,4-tetrahydro-8,9-dihydroxy-3-(2-piperidinoethyl)-5H-[1]benzopyrano[3,4-c]pyridin-5-one, 0.022 m of diethylsulfate and 0.1 m K2CO3 in 250 cc of acetone was refluxed for 20 hr and filtered hot. After evaporation, the residue was crystallized twice from EtOAc affording 0.6 g of product; mp 144°-146° C.

Workup

  1. temperaturewas refluxed for 20 hr
  2. filtrationfiltered hot
  3. customAfter evaporation
  4. customthe residue was crystallized twice from EtOAc affording 0.6 g of product

Sources & evidence

ORD record
ord-5a1cdb341e104ba390d47f3bdaaf7afc
Source dataset
uspto-grants-1976_03
Patent number
US03946008

Reaction notes

Loading…