N-[7-(1-acetyl-1,2,3,6-tetrahydro-pyridin-4-yl)-4-methoxy-benzothiazol-2-yl]-4-fluoro-benzamide → N-[7-(1-acetyl-piperidin-4-yl)-4-methoxy-benzothiazol-2-yl]-4-fluoro-benzamide

HRID 1582118Notes

Reaction equation

HRID 1582118 reaction equation
[C:1]([N:4]1[CH2:9][CH:8]=[C:7]([C:10]2[C:18]3[S:17][C:16]([NH:19][C:20](=[O:28])[C:21]4[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)=[N:15][C:14]=3[C:13]([O:29][CH3:30])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]>CO.[Pd]>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[C:18]3[S:17][C:16]([NH:19][C:20](=[O:28])[C:21]4[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=4)=[N:15][C:14]=3[C:13]([O:29][CH3:30])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 10287935N-[7-(1-acetyl-1,2,3,6-tetrahydro-pyridin-4-yl)-4-methoxy-benzothiazol-2-yl]-4-fluoro-benzamide

Product 1

HCID 10194734N-[7-(1-acetyl-piperidin-4-yl)-4-methoxy-benzothiazol-2-yl]-4-fluoro-benzamideYield 52%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 0.04 g (0.94 mMol) of N-[7-(1-acetyl-1,2,3,6-tetrahydro-pyridin-4-yl)-4-methoxy-benzothiazol-2-yl]-4-fluoro-benzamide in 2.0 ml of methanol 10.0 mg of Pd/C (10%) were added. This reaction mixture was hydrogenated at 60° C. for 6 h, then filtered and evaporated to dryness in vacuo to yield 0.021 g (52%) N-[7-(1-acetyl-piperidin-4-yl)-4-methoxy-benzothiazol-2-yl]-4-fluoro-benzamide as a white solid. F.p.: 225-233° C.

Workup

  1. filtrationfiltered
  2. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-8a63d680d7274c6e914a029fb3f3b634
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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