Potassium Carbonate → 1,1-dimethylethyl 4-[4-[[methyl[(1R)-1,2,3,4-tetrahydro-1-naphthalenyl]amino]methyl]-2-thiazolyl]-1-piperidinecarboxylate

HRID 660039Notes

Reaction equation

HRID 660039 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[S:6][CH:7]=1.[CH3:21][NH:22][C@H:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:21][N:22]([CH2:2][C:3]1[N:4]=[C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[S:6][CH:7]=1)[C@H:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 7128544(R)-N-Methyl-1,2,3,4-tetrahydronaphthalen-1-amineHCID 57423790Tert-butyl 4-[4-(chloromethyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate2×

Product 1

HCID 685273541,1-dimethylethyl 4-[4-[[methyl[(1R)-1,2,3,4-tetrahydro-1-naphthalenyl]amino]methyl]-2-thiazolyl]-1-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(1,1-dimethylethyl) 4-(4-chloromethyl-2-thiazolyl)-1-piperidinecarboxylate (i.e. the product of Example 1, Step C) (0.15 g, 0.47 mmol), (1R)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine (0.076 g, 0.47 mmol) and potassium carbonate (0.072 g, 0.52 mmol) in dry acetonitrile (5 mL) was heated at reflux for two days. Then the reaction mixture was filtered, concentrated under reduced pressure, diluted with dichloromethane, and washed with 1 N aqueous hydrochloric acid and water. The organic layers were dried (MgSO4) and concentrated under reduced pressure to give 0.19 g of the title compound as a tan foam.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for two days
  3. filtrationThen the reaction mixture was filtered
  4. concentrationconcentrated under reduced pressure
  5. additiondiluted with dichloromethane
  6. washwashed with 1 N aqueous hydrochloric acid and water
  7. dry with materialThe organic layers were dried (MgSO4)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cdc1afbb831c4d3ab017758a5d2e8ed3
Source dataset
uspto-grants-2011_12
Patent number
US08084468B2

Reaction notes

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