Morpholine-4-carboxylic acid [7-(1-acetyl-1,2,3,6-tetrahydro-pyridin-4-yl)-4-methoxy-benzothiazol-2-yl]-amide → Morpholine-4-carboxylic acid [7-(1-acetyl-piperidin-4-yl)-4-methoxy-benzothiazol-2-yl]-amide

HRID 1582122Notes

Reaction equation

HRID 1582122 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]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[O:21])=[N:15][C:14]=3[C:13]([O:28][CH3:29])=[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]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[O:21])=[N:15][C:14]=3[C:13]([O:28][CH3:29])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 86588836Morpholine-4-carboxylic acid [7-(1-acetyl-1,2,3,6-tetrahydro-pyridin-4-yl)-4-methoxy-benzothiazol-2-yl]-amide

Product 1

HCID 10309977Morpholine-4-carboxylic acid [7-(1-acetyl-piperidin-4-yl)-4-methoxy-benzothiazol-2-yl]-amideYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 0.03 g (0.72 mmol) of morpholine-4-carboxylic acid [7-(1-acetyl-1,2,3,6-tetrahydro-pyridin-4-yl)-4-methoxy-benzothiazol-2-yl]-amide in 2.0 ml of methanol 10.0 mg of Pd/C (10%) were added. The reaction mixture was hydrogenated at 60° C. for 6 h, then filtered and evaporated to dryness in vacuo to yield 0.024 g (80%) morpholine-4-carboxylic acid [7-(1-acetyl-piperidin-4-yl)-4-methoxy-benzothiazol-2-yl]-amide as a white solid. F.p.: 196° C. (dec.).

Workup

  1. filtrationfiltered
  2. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-5cec550a2843490c884eaf0a8d8600c5
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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