Trifluoroacetic acid → [1-(Methylsulfonyl)piperidin-4-yl]amine trifluoroacetate

HRID 30103Notes

Reaction equation

HRID 30103 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10][CH2:9]1)(C)(C)C.[F:19][C:20]([F:25])([F:24])[C:21]([OH:23])=[O:22]>C(Cl)Cl>[F:19][C:20]([F:25])([F:24])[C:21]([OH:23])=[O:22].[CH3:17][S:14]([N:11]1[CH2:10][CH2:9][CH:8]([NH2:7])[CH2:13][CH2:12]1)(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 25250149tert-Butyl [1-(methanesulfonyl)piperidin-4-yl]carbamate

Product 1

HCID 11975076[1-(Methylsulfonyl)piperidin-4-yl]amine trifluoroacetateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of (1-methanesulfonyl-piperidin-4-yl)-carbamic acid tert-butyl ester (1.14 g, 4.1 mmol, from above) in methylene chloride (15 mL) was treated at room temperature with trifluoroacetic acid (5.3 mL). After stirring for 2 hours, all solvent was removed and the residue was triturated with ether. This was filtered, washed with ether and dried in vacuum to give 1-methanesulfonyl-piperidin-4-ylamine; compound with trifluoro-acetic acid (1.20 g, 100% yield). HRMS, observed: 177.0692; Calcd for M+: 177.0698.

Workup

  1. customall solvent was removed
  2. customthe residue was triturated with ether
  3. filtrationThis was filtered
  4. washwashed with ether
  5. customdried in vacuum

Sources & evidence

ORD record
ord-74e5a278559740078390b7de6cb938b2
Source dataset
uspto-grants-2008_09
Patent number
US07423051B2

Reaction notes

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