Sulfuric Acid → Sulfate Ion

HRID 563932Notes

Reaction equation

HRID 563932 reaction equation
[CH2:1]([C:8]1([OH:31])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][NH:16][C:17]([NH:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=[C:22]([CH3:30])[CH:21]=2)=[O:18])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:32][S:33]([OH:36])(=[O:35])=[O:34]>CO>[CH2:1]([C:8]1([OH:31])[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][NH:16][C:17]([NH:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=[C:22]([CH3:30])[CH:21]=2)=[O:18])[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:33]([O-:36])([O-:35])(=[O:34])=[O:32]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 10173280Palosuran

Product 2

HCID 1117Sulfate IonHCID 10173280Palosuran

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-2 °C

Procedure

To a suspension of 1-[2-(4-benzyl-4-hydroxy-piperidin-1-yl)-ethyl]-3-(2-methyl-quinolin-4-yl)-urea (21.36 kg) in CH3OH (178 L) is added aqueous H2SO4 (6 L, 9.91%) during 10 min. The clear solution is filtered and further aqueous H2SO4 (33.8 L, 1.07 M) is added during 45 min. The solution is cooled to −2° C. during 1.5 h and stirred at −5 to −9° C. for 1 h. The formed precipitate is filtered, washed with cooled CH3OH (−5° C., 54 L) and dried under a stream of nitrogen provide 1-[2-(4-benzyl-4-hydroxy-piperidin-1-yl)-ethyl]-3-(2-methyl-quinolin-4-yl)-urea of formula I sulfate as a non-defined hydrate. The so obtained salt is exposed to humid atmosphere (>70% RH) at 25° C. to provide the title compound.

Workup

  1. filtrationThe clear solution is filtered
  2. additionfurther aqueous H2SO4 (33.8 L, 1.07 M) is added during 45 min
  3. filtrationThe formed precipitate is filtered
  4. washwashed with cooled CH3OH (−5° C., 54 L)
  5. customdried under a stream of nitrogen

Sources & evidence

ORD record
ord-52a5fe55fbdd4dda81775bc28c9d2c00
Source dataset
uspto-grants-2011_11
Patent number
US08067601B2

Reaction notes

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