Methanesulfonic Acid → 4-({1-[2-(4-Cyanophenyl)ethyl]-4-hydroxypiperidin-4-ylmethyl}methylamino)benzoic acid monomethanesulfonate

HRID 1727104Notes

Reaction equation

HRID 1727104 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[C:6]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][C:19]([CH2:23][N:24]([CH3:34])[C:25]3[CH:33]=[CH:32][C:28]([C:29]([OH:31])=[O:30])=[CH:27][CH:26]=3)([OH:22])[CH2:18][CH2:17]2)=[CH:10][CH:9]=1)#[N:7]>O>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[C:6]([C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][C:19]([CH2:23][N:24]([CH3:34])[C:25]3[CH:26]=[CH:27][C:28]([C:29]([OH:31])=[O:30])=[CH:32][CH:33]=3)([OH:22])[CH2:20][CH2:21]2)=[CH:12][CH:13]=1)#[N:7]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 12986481UP9V9DB2RD

Product 1

HCID 866033484-({1-[2-(4-Cyanophenyl)ethyl]-4-hydroxypiperidin-4-ylmethyl}methylamino)benzoic acid monomethanesulfonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methanesulfonic acid (1.42 mL) was added to a suspension of the compound (7.2 g) obtained in Example 1 in water (50 mL), was heated with stirring until the compound was dissolved, followed by cooling to room temperature with stirring. The crystals were collected by filtration and were recrystallized from water (50 mL). The resulting crystals were collected by filtration, washed with acetone, and dried under reduced pressure to yield the titled compound (7.6 g) as crystals.

Workup

  1. temperaturewas heated
  2. dissolutionwas dissolved
  3. stirringwith stirring
  4. filtrationThe crystals were collected by filtration
  5. customwere recrystallized from water (50 mL)
  6. filtrationThe resulting crystals were collected by filtration
  7. washwashed with acetone
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-5dc419a3ae4b4cd88ac5cdc37ac19b4c
Source dataset
uspto-grants-2009_02
Patent number
US07494987B2

Reaction notes

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