Piperidin-4-ol → HCID 13044293, compound

HRID 434686Notes

Reaction equation

HRID 434686 reaction equation
Cl[C:2]1[C:13]2=[C:14]3[N:9]([CH:10]([CH3:15])[CH2:11][CH2:12]2)[CH:8]=[C:7]([C:16]([OH:18])=[O:17])[C:6](=[O:19])[C:5]3=[CH:4][CH:3]=1.[OH:20][CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>CN1CCCC1=O>[OH:20][CH:21]1[CH2:26][CH2:25][N:24]([C:2]2[C:13]3=[C:14]4[N:9]([CH:10]([CH3:15])[CH2:11][CH2:12]3)[CH:8]=[C:7]([C:16]([OH:18])=[O:17])[C:6](=[O:19])[C:5]4=[CH:4][CH:3]=2)[CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 79341Piperidin-4-olHCID 20259004HCID 20259004, compound

Product 1

HCID 13044293HCID 13044293, compoundYield 23.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In a 100 ml flask were placed 6.1 g of 8-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid, 9.5 g of 4-hydroxypiperidine and 60 ml of N-methylpyrrolidone and the mixture was stirred at 150° C. in an argon gas atmosphere. After 6 hours, N-methylpyrrolidone and excessive 4-hydroxypiperidine were removed under reduced pressure. To the residue were added dimethylformamide, ethanol and water and allowed to stand overnight to give 2.3 g of crude crystals which were recrystallized from ethanol-water to give 1.8 g of 8-(4-hydroxy-1-piperidyl)-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid. m.p. 238°-240° C.

Workup

  1. customIn a 100 ml flask were placed
  2. customN-methylpyrrolidone and excessive 4-hydroxypiperidine were removed under reduced pressure
  3. additionTo the residue were added dimethylformamide, ethanol and water
  4. waitto stand overnight
  5. customto give 2.3 g of crude crystals which
  6. customwere recrystallized from ethanol-water

Sources & evidence

ORD record
ord-3dbfa58284d64bfbbb6e0afbaa84d8c3
Source dataset
uspto-grants-1983_08
Patent number
US04399134

Reaction notes

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