Hydrochloric Acid → Piboserod hydrochloride

HRID 1871039Notes

Reaction equation

HRID 1871039 reaction equation
[CH2:1]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][NH:12][C:13]([C:15]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]3[CH2:24][CH2:25][CH2:26][O:27][C:16]=23)=[O:14])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].[ClH:28]>C(O)C>[ClH:28].[CH2:1]([N:5]1[CH2:6][CH2:7][CH:8]([CH2:11][NH:12][C:13]([C:15]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]3[CH2:24][CH2:25][CH2:26][O:27][C:16]=23)=[O:14])[CH2:9][CH2:10]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 177336Piboserod

Product 1

HCID 177335Piboserod hydrochlorideYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Method B N-[(1-Butyl-4-piperidinyl)methyl]-3,4-dihydro-2H-[1,3]-oxazino[3,2-a]indole-10-carboxamide (SB-207266) (100 g, 0.27 mol) was dissolved in ethanol (870 ml) and the resulting solution filtered to remove particulates. Anhydrous HCl in ethanol (83 ml, 3.6M, 0.30 mol) was added causing the product to precipitate out of solution. The slurry was heated to redissolve the solid and hexane (550 ml) was added. After cooling to room temperature, the mixture was cooled to 0-5° C. and stirred at that temperature for about two hours. The solid was isolated by filtration and dried in vacuo at about 40° C. to give the product, N-[(1-butyl-4-piperidinyl)methyl]-3,4-dihydro-2H-[1,3]-oxazino [3,2-a]indole-10-carboxamide hydrochloride, (102.8 g) in 94% yield.

Workup

  1. filtrationthe resulting solution filtered
  2. customto remove particulates
  3. customto precipitate out of solution
  4. temperatureThe slurry was heated
  5. dissolutionto redissolve the solid and hexane (550 ml)
  6. additionwas added
  7. temperaturethe mixture was cooled to 0-5° C.
  8. customThe solid was isolated by filtration
  9. customdried in vacuo at about 40° C.

Sources & evidence

ORD record
ord-75d6dd5013244945936688bf675d51c1
Source dataset
uspto-grants-2000_08
Patent number
US06100397

Reaction notes

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