Trifluoroacetic acid → Trifluoro-methanesulfonic acid 7-(piperidin-4-ylmethyl-propyl-amino)-5,6,7,8-tetrahydro-naphthalen-2-yl ester

HRID 983482Notes

Reaction equation

HRID 983482 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]([CH2:34][CH2:35][CH3:36])[CH:16]2[CH2:25][CH2:24][C:23]3[C:18](=[CH:19][C:20]([O:26][S:27]([C:30]([F:33])([F:32])[F:31])(=[O:29])=[O:28])=[CH:21][CH:22]=3)[CH2:17]2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]([CH2:34][CH2:35][CH3:36])[CH:16]2[CH2:17][C:18]3[CH:19]=[C:20]([O:26][S:27]([C:30]([F:33])([F:31])[F:32])(=[O:29])=[O:28])[CH:21]=[CH:22][C:23]=3[CH2:24][CH2:25]2)[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 865890904-{[Propyl-(7-trifluoromethanesulfonyloxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-amino]-methyl}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 21362810Trifluoro-methanesulfonic acid 7-(piperidin-4-ylmethyl-propyl-amino)-5,6,7,8-tetrahydro-naphthalen-2-yl esterYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{[propyl-(7-trifluoromethanesulfonyloxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-amino]-methyl}-piperidine-1-carboxylic acid tert-butyl ester, (220 mg, 0.41 mmol) in methylene chloride (5.0 mL) under an inert atmosphere was added trifluoroacetic acid (1.0 ml). The reaction was stirred at room temperature for 1 h. The reaction was concentrated in-vacuo and partitioned between 1 N NaOH (20 ml) and EtOAc (30 ml). The organic layer was separated, dried (MgSO4), and concentrated to afford trifluoro-methanesulfonic acid 7-(piperidin-4-ylmethyl-propyl-amino)-5,6,7,8-tetrahydro-naphthalen-2-yl ester (114mg).

Workup

  1. concentrationThe reaction was concentrated in-vacuo
  2. custompartitioned between 1 N NaOH (20 ml) and EtOAc (30 ml)
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b914a46c0058442c92dde17f37bd04e3
Source dataset
uspto-grants-2005_03
Patent number
US06864266B2

Reaction notes

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