Acetone → HCID 86758144, compound

HRID 2186343Notes

Reaction equation

HRID 2186343 reaction equation
S(Cl)([Cl:3])=O.C[C:6](C)=[O:7].C(=O)=O.[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[N:20]=[CH:19][CH:18]=[C:17]2[CH2:24][CH2:25][CH2:26][C@@H:27]1[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][C@@H:28]1[C:40]([OH:42])=O>CO>[ClH:3].[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[N:20]=[CH:19][CH:18]=[C:17]2[CH2:24][CH2:25][CH2:26][C@@H:27]1[CH2:32][CH2:31][NH:30][CH2:29][C@@H:28]1[C:40]([O:7][CH3:6])=[O:42]

Participants

6

Reactant 4

HCID 180AcetoneHCID 280Carbon DioxideHCID 24386Thionyl ChlorideHCID 70174960HCID 70174960, compound

Product 1

HCID 86758144HCID 86758144, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2 cm3 of thionyl chloride were added dropwise to a stirred suspension, cooled to a temperature in the region of −30° C. with a cooling bath of acetone and solid carbon dioxide, of 4.29 g of (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxy-carbonyl)piperidine-3-carboxylic acid in 50 cm3 of methanol. The solution obtained was brought to a temperature in the region of 20° C. and the reaction mixture was stirred for 16 hours at this temperature. After evaporating the solution under reduced pressure (5 kPa) at a temperature in the region of 40 ° C., the residue obtained was triturated in approximately 30 cm3 of diisopropyl ether. The crystals obtained were filtered off, washed with 2 times 10 cm3 of diisopropyl ether, and then dried in the air. 4.20 g of methyl (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate hydrochloride were obtained in the form of a solid with a light yellow color which melts with softening at a temperature in the region of 140° C.

Workup

  1. customThe solution obtained
  2. customwas brought to a temperature in the region of 20° C.
  3. customAfter evaporating the solution under reduced pressure (5 kPa) at a temperature in the region of 40 ° C.
  4. customthe residue obtained
  5. customwas triturated in approximately 30 cm3 of diisopropyl ether
  6. customThe crystals obtained
  7. filtrationwere filtered off
  8. washwashed with 2 times 10 cm3 of diisopropyl ether
  9. customdried in the air

Sources & evidence

ORD record
ord-fe05cf8702bf44a2a71c8613f6c54dbd
Source dataset
uspto-grants-2002_06
Patent number
US06403610B1

Reaction notes

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