Hydrochloric Acid → 1-Benzoyl-3-[1-(2-[1,4-benzodioxan-2-yl]-2-hydroxyethyl)piperid-4-yl]-urea

HRID 225144Notes

Reaction equation

HRID 225144 reaction equation
[C:1]([NH:9][C:10]([NH:12][CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]([CH:22]2[O:27][C:26]3[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=3[O:24][CH2:23]2)=[O:21])[CH2:15][CH2:14]1)=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O.Cl>CO.[OH-].[Na+]>[C:1]([NH:9][C:10]([NH:12][CH:13]1[CH2:14][CH2:15][N:16]([CH2:19][CH:20]([CH:22]2[O:27][C:26]3[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=3[O:24][CH2:23]2)[OH:21])[CH2:17][CH2:18]1)=[O:11])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 126085861-Benzoyl-3-[1-(2-[1,4-benzodioxan-2-yl]-2-oxoethyl)piperid-4-yl]-urea

Product 1

HCID 126085921-Benzoyl-3-[1-(2-[1,4-benzodioxan-2-yl]-2-hydroxyethyl)piperid-4-yl]-urea

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

1-Benzoyl-3-[1-(2-[1,4-benzodioxan-2-yl]-2-oxoethyl)piperid-4-yl]-urea (7.21 g, 0.017 mol) was suspended in methanol (80 cm3) and was stirred at room temperature. Sodium borohydride (1.0 g, 0.026 mol) in 2N sodium hydroxide (10 cm3) was added dropwise to the stirring solution and then left to stir for a further hour. Water was added and the solid filtered off and dried (5.41 g, 75%). A. T.L.C. of a small portion of the solid was run in freshly prepared toluene: ethanol: 0.880 ammonia (90:10:1 by volume) on a silica plate and was found to contain two components having RF values of about 0.30 and 0.34. The solid was recrystallised from n-butyl acetate (9 times) to give the component (1.19 g) with the lower RF value. This was suspended in a small amount of methanol and ethanolic HCl added until the solution was just acidic. The hydrochloride of the title compound (0.96 g, 74%) was collected.

Workup

  1. waitleft
  2. stirringto stir for a further hour
  3. filtrationthe solid filtered off
  4. customdried (5.41 g, 75%)
  5. customThe solid was recrystallised from n-butyl acetate (9 times)
  6. customto give the component (1.19 g) with the lower RF value
  7. additionadded until the solution
  8. customThe hydrochloride of the title compound (0.96 g, 74%) was collected

Sources & evidence

ORD record
ord-0309968e12cb464eb994a24632eb2221
Source dataset
uspto-grants-1980_11
Patent number
US04235915

Reaction notes

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