Dimethylformamide → HCID 19878329, compound

HRID 1885912Notes

Reaction equation

HRID 1885912 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]4=3)[C:14]3[C:9]2=[CH:10][C:11]([O:25][CH3:26])=[CH:12][CH:13]=3)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.Cl.Cl[CH2:40][CH2:41][N:42]1[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1>[Cl-].[Na+].O>[CH3:26][O:25][C:11]1[CH:10]=[C:9]2[C:14]([C:15]3[C:20]([CH:8]2[C:5]2[CH:4]=[CH:3][C:2]([O:1][CH2:40][CH2:41][N:42]4[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]4)=[CH:7][CH:6]=2)=[C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]2=[CH:17][CH:16]=3)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 19878336HCID 19878336, compound

Product 1

HCID 19878329HCID 19878329, compound

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

Five g of the compound of Example 1 was combined with 10.9 g of potassium carbonate, 50 ml of dimethylformamide, and 2.9 g of 1-(2-chloroethyl)piperdine hydrochloride. The mixture was stirred under reflux for 1 hour under nitrogen, and it was then cooled and poured into 1500 ml of iced brine. The aqueous mixture was extracted 3 times with 200 ml portions of ethyl acetate, and the organic extract was washed 3 times with 25 ml portions of brine, dried and evaporated under vacuum to obtain 6.6 g of tan crystals. The impure product was purified by high performance liquid chromatography over silica gel, using 2% triethylamine and diethyl ether. The product-containing fractions were concentrated under vacuum to obtain 5.43 g of white crystals, which were recrystallized from 60 ml of acetone to obtain 3.95 g of pure product, m.p. 147°-148° C.

Workup

  1. temperatureunder reflux for 1 hour under nitrogen
  2. temperatureit was then cooled
  3. extractionThe aqueous mixture was extracted 3 times with 200 ml portions of ethyl acetate
  4. extractionthe organic extract
  5. washwas washed 3 times with 25 ml portions of brine
  6. customdried
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-0b483c32e68f40ee9948c60edeaebde4
Source dataset
uspto-grants-1992_09
Patent number
US05147880

Reaction notes

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