Water → HCID 86627793, compound

HRID 645496Notes

Reaction equation

HRID 645496 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][C:17]2[CH:22]=[C:21]([Cl:23])[N:20]=[C:19](S(C)(=O)=O)[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C-:28]#[N:29].[Na+].O>C(Cl)Cl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][C:17]2[CH:22]=[C:21]([Cl:23])[N:20]=[C:19]([C:28]#[N:29])[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 962Water2×HCID 8929Sodium CyanideHCID 86627794HCID 86627794, compound

Product 1

HCID 86627793HCID 86627793, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of the crude 4-[2-(6-chloro-2-methanesulfonylpyrimidin-4-yl oxy)ethyl]-piperidine-1-carboxylic acid tert-butyl ester (4.9 g) and NaCN (14 mmol) in CH2Cl2:H2O (50 mL, 4:1) is added TBAB (tetrabutylammonium bromide) (0.06 mmol) at room temperature. After stirring at the same temperature for 10 h, TBAB (0.19 mml) is added to the reaction mixture. The reaction mixture is stirred at room temperature for 2 h and H2O is added. The organic layer is separated, dried over MgSO4 and evaporated in vacuo. The resulting residue is purified by silica gel column chromatography to give 4-[2-(6-chloro-2-cyanopyrimidin-4-yloxy)ethyl]piperidine-1-carboxylic acid tert-butyl ester; 1H-NMR (CDCl3), δ: 1.14-1.28 (2H, m), 1.45 (9H, s), 1.56-1.78 (7H, m), 2.69 (2H, t), 4.11 (2H, m), 4.49 (2H, t), 6.93 (1H, s).

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 2 h
  2. customThe organic layer is separated
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c3851208468c4361a534e8fa057666fc
Source dataset
uspto-grants-2010_04
Patent number
US07704996B2

Reaction notes

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