Hydrochloric Acid → 8-[3-(4-piperidinyl)propanoyl]1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one

HRID 1816030Notes

Reaction equation

HRID 1816030 reaction equation
C([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][C:12]([C:14]2[CH:15]=[C:16]3[C:21]4=[C:22]([CH2:24][CH2:25][N:20]4[C:19](=[O:26])[CH2:18][CH2:17]3)[CH:23]=2)=[O:13])[CH2:6][CH2:5]1)(=O)C.Cl>C1(C)C=CC=CC=1>[NH:4]1[CH2:5][CH2:6][CH:7]([CH2:10][CH2:11][C:12]([C:14]2[CH:15]=[C:16]3[C:21]4=[C:22]([CH2:24][CH2:25][N:20]4[C:19](=[O:26])[CH2:18][CH2:17]3)[CH:23]=2)=[O:13])[CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10291701HCID 10291701, compound

Product 1

HCID 99665448-[3-(4-piperidinyl)propanoyl]1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-oneYield 97.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

8-[3-(1-acetyl-4-piperidinyl)-1-oxopropyl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinoline-4-one (10 g, 28.2 mmol) and 2 N hydrochloric acid (50 mL) were stirred at about 90° C. for 8 hours. After cooled to about 25° C., toluene (30 mL) was added to the reaction mixture, the layers were separated, and 30% aqueous sodium hydroxide solution (16 mL) was added to the aqueous layer to adjust pH to 13.8. A mixture of toluene-acetonitrile (1:1) (50 mL) was added thereto, and the layers were separated. A mixture of toluene-acetonitrile (1:1) (50 mL) was added to aqueous layer, and the layers were separated. The organic layers were combined, 30% brine (30 mL) was added, and the layers were separated. The organic layer was concentrated under reduced pressure to obtain 8.55 g (yield 92.5%) of the desired compound as a solid.

Workup

  1. customthe layers were separated
  2. addition30% aqueous sodium hydroxide solution (16 mL) was added to the aqueous layer
  3. additionA mixture of toluene-acetonitrile (1:1) (50 mL)
  4. additionwas added
  5. customthe layers were separated
  6. additionA mixture of toluene-acetonitrile (1:1) (50 mL)
  7. additionwas added to aqueous layer
  8. customthe layers were separated
  9. addition30% brine (30 mL) was added
  10. customthe layers were separated
  11. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-51e7f0f29fc443eeb7927a0f687f0ffb
Source dataset
uspto-grants-2005_04
Patent number
US06881842B2

Reaction notes

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