Heptane → Methyl-phenyl-carbamic Acid 4,4-dimethyl-3,4,5,6-tetrahydro-2H-[1,3']bipyridinyl-6'-yl Ester

HRID 1179949Notes

Reaction equation

HRID 1179949 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[N:10][C:11]([OH:14])=[CH:12][CH:13]=2)[CH2:4][CH2:3]1.[CH3:16][N:17]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:18](Cl)=[O:19].N12CCN(CC1)CC2.CCCCCCC>ClCCl>[CH3:1][C:2]1([CH3:15])[CH2:3][CH2:4][N:5]([C:8]2[CH:9]=[N:10][C:11]([O:14][C:18](=[O:19])[N:17]([CH3:16])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:12][CH:13]=2)[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 8900HeptaneHCID 9237DabcoHCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 178426342HCID 178426342, compound

Product 1

HCID 69520090Methyl-phenyl-carbamic Acid 4,4-dimethyl-3,4,5,6-tetrahydro-2H-[1,3']bipyridinyl-6'-yl EsterYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4,4-dimethyl-3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-6′-ol (0.86 g, 4.17 mmol), N-methyl-N-phenylcarbamoyl chloride (0.71 g, 4.17 mmol) and 1,4-diazabicyclo[2,2,2]octane (0.47 g, 4.17 mmol) in dichloromethane (10 mL) was stirred at room temperature for 2 hours. Extra dichloromethane was added and the solution was washed with water, dried over sodium sulphate, filtered and evaporated in vacuo. Crystallisation from ethyl acetate:heptane yielded the title compound (0.58 g, 41% yield)

Workup

  1. washthe solution was washed with water
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customCrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-668d9027acfe419ca9833f0e479a8963
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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