Trifluoroacetic acid → N-[7-(ethyl-piperidin-4-ylmethyl-amino)-5,6,7,8-tetrahydro-naphthalen-2-yl]-4-methanesulfonyl-benzamide

HRID 983458Notes

Reaction equation

HRID 983458 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]([CH2:39][CH3:40])[CH:16]2[CH2:25][CH2:24][C:23]3[C:18](=[CH:19][C:20]([NH:26][C:27](=[O:38])[C:28]4[CH:33]=[CH:32][C:31]([S:34]([CH3:37])(=[O:36])=[O:35])=[CH:30][CH:29]=4)=[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>[CH2:39]([N:15]([CH2:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[CH:16]1[CH2:17][C:18]2[CH:19]=[C:20]([NH:26][C:27](=[O:38])[C:28]3[CH:33]=[CH:32][C:31]([S:34]([CH3:37])(=[O:35])=[O:36])=[CH:30][CH:29]=3)[CH:21]=[CH:22][C:23]=2[CH2:24][CH2:25]1)[CH3:40]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 686234154-({Ethyl-[7-(4-methanesulfonyl-benzoylamino)-1,2,3,4-tetrahydro-naphthalen-2-yl]-amino}-methyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 11248400N-[7-(ethyl-piperidin-4-ylmethyl-amino)-5,6,7,8-tetrahydro-naphthalen-2-yl]-4-methanesulfonyl-benzamideYield 94.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-({ethyl-[7-(4-methanesulfonyl-benzoylamino)-1,2,3,4-tetrahydro-naphthalen-2-yl]-amino}-methyl)-piperidine-1-carboxylic acid tert-butyl ester (1.33 g, 2.3 mmol) in methylene chloride (30 mL) under a nitrogen atmosphere was added trifluoroacetic acid (10 mL). The reaction was stirred at room temperature for 30 min. and concentrated in-vacuo. The residue was partitioned between EtOAc (50 mL) and 10% aq. KOH (50 mL), the organic layer was separated, dried over MgSO4, filtered, and concentrated to afford N-[7-(ethyl-piperidin-4-ylmethyl-amino)-5,6,7,8-tetrahydro-naphthalen-2-yl]-4-methanesulfonyl-benzamide (1.02 g). [M+H]+=470.

Workup

  1. concentrationconcentrated in-vacuo
  2. customThe residue was partitioned between EtOAc (50 mL) and 10% aq. KOH (50 mL)
  3. customthe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f3a049c49ffb4f99911421afe4a4a7ea
Source dataset
uspto-grants-2005_03
Patent number
US06864266B2

Reaction notes

Loading…