Hydrochloric Acid → HCID 70172163, compound

HRID 2186369Notes

Reaction equation

HRID 2186369 reaction equation
[F:1][CH:2]([C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([O:33][CH3:34])[CH:31]=2)[N:26]=[CH:25][CH:24]=1)[CH2:3][CH2:4][C@@H:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][S:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)[CH2:7][C@@H:6]1[C:19]([O:21]C)=[O:20].[ClH:35]>C(OC(C)C)(C)C>[ClH:35].[ClH:35].[F:1][CH:2]([C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([O:33][CH3:34])[CH:31]=2)[N:26]=[CH:25][CH:24]=1)[CH2:3][CH2:4][C@@H:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][S:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)[CH2:7][C@@H:6]1[C:19]([OH:21])=[O:20]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131723278HCID 131723278, compound

Product 1

HCID 70172163HCID 70172163, compound

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 0.2 g of methyl (3R,4R)-4-[3-(R,S)-fluoro-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(2-thienylthio)ethyl]piperidine-3-carboxylate in 3 cm3 of 6N aqueous hydrochloric acid was heated with stirring at a temperature in the region of 100° C. for 7 hours and then evaporated under reduced pressure (5 kPa) at a temperature in the region of 50° C. The residue obtained was stirred in 10 cm3 of diisopropyl ether. The crystals which resulted therefrom were filtered off, washed with 2 times 5 cm3 of diisopropyl ether, and dried under reduced pressure (13 Pa) at a temperature in the region of 60° C. 0.22 g of (3R,4R)-4-[3-(R,S)-fluoro-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(2-thienylthio)ethyl]piperidine-3-carboxylic acid dihydrochloride were obtained in the form of a solid with a beige color melting with softening at a temperature in the region of 140° C.

Workup

  1. customevaporated under reduced pressure (5 kPa) at a temperature in the region of 50° C
  2. customThe residue obtained
  3. customThe crystals which resulted
  4. filtrationtherefrom were filtered off
  5. washwashed with 2 times 5 cm3 of diisopropyl ether
  6. customdried under reduced pressure (13 Pa) at a temperature in the region of 60° C

Sources & evidence

ORD record
ord-a026272103784df9870f53edeb791f71
Source dataset
uspto-grants-2002_06
Patent number
US06403610B1

Reaction notes

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