Cyclohexane → Ethyl 1-(2-chloroethyl)-4-[3-(3-fluoroquinolin-4-yl)propyl]piperidine-4-carboxylate monohydrochloride

HRID 395002Notes

Reaction equation

HRID 395002 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[CH2:16][CH2:17][CH2:18][C:19]1([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:24][CH2:23][N:22]([CH2:25][CH2:26]O)[CH2:21][CH2:20]1)=[CH:13][CH:12]=[CH:11][CH:10]=2.C1CCCCC1>ClCCl>[ClH:3].[Cl:3][CH2:26][CH2:25][N:22]1[CH2:23][CH2:24][C:19]([CH2:18][CH2:17][CH2:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=[CH:7][C:6]=2[F:5])([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 8078CyclohexaneHCID 24386Thionyl ChlorideHCID 22468935Ethyl 4-[3-(3-fluoroquinolin-4-yl)-propyl]-1-(2-hydroxyethyl)piperidine-4-carboxylate

Product 1

HCID 22468779Ethyl 1-(2-chloroethyl)-4-[3-(3-fluoroquinolin-4-yl)propyl]piperidine-4-carboxylate monohydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

1.2 cm3 of thionyl chloride in 5 cm3 of dichloromethane were added to a solution of 1.55 g of ethyl 4-[3-(3-fluoroquinolin-4-yl)propyl]-1-(2-hydroxy-ethyl)piperidine-4-carboxylate in 35 cm3 of dichloromethane, with stirring at a temperature in the region of 20° C. After stirring for 42 hours at a temperature in the region of 20° C., the reaction mixture was concentrated to dryness under reduced pressure (1.2 kPa) at about 50° C. The foam obtained was taken up in 3 times 100 cm3 of cyclohexane, concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. and oven-dried under reduced pressure (10 kPa) at a temperature in the region of 20° C. 1.8 g of ethyl 1-(2-chloroethyl)-4-[3-(3-fluoroquinolin-4-yl)propyl]piperidine-4-carboxylate monohydrochloride were obtained in the form of a cream-colored solid.

Workup

  1. stirringAfter stirring for 42 hours at a temperature in the region of 20° C.
  2. concentrationthe reaction mixture was concentrated to dryness under reduced pressure (1.2 kPa) at about 50° C
  3. customThe foam obtained
  4. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C.
  5. customoven-dried under reduced pressure (10 kPa) at a temperature in the region of 20° C

Sources & evidence

ORD record
ord-fe50977b82214ca4a6ea94e01dfe3ce5
Source dataset
uspto-grants-2003_08
Patent number
US06603005B2

Reaction notes

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