4-(3,4-Dichlorophenoxy)piperidine → tert-Butyl 2-{[4-(3,4-dichlorophenoxy)piperidin-1-yl}methyl]morpholine-4-carboxylate

HRID 2110804Notes

Reaction equation

HRID 2110804 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[Cl:15])[O:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.CS(O[CH2:21][C:22]1(CO)[O:27][CH2:26][CH2:25][N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:23]1)(=O)=O>C(#N)C>[NH3:9].[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[Cl:15])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:21][CH:22]2[O:27][CH2:26][CH2:25][N:24]([C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[CH2:23]2)[CH2:8][CH2:7]1

Participants

5

Reactant 2

HCID 37320424-(3,4-Dichlorophenoxy)piperidineHCID 866286481,1-Dimethylethyl 2-[[(methylsulfonyl)oxy]methyl]-2-(hydroxymethyl)-4-morpholinecarboxylate

Product 2

HCID 222AmmoniaHCID 17974804tert-Butyl 2-{[4-(3,4-dichlorophenoxy)piperidin-1-yl}methyl]morpholine-4-carboxylateYield 76.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(3,4-dichlorophenoxy)piperidine (WO 01/77101; 9.22 g) dissolved in acetonitrile (60 ml) was added the product of Step (a) (5.53 g). The mixture was refluxed for 12 hrs and the solvents were evaporated. Purification by flash chromatography eluting with dichloromethane:methanol:NH3 (aq) (2:97.9:0.1) gave the sub-title compound as an oil (5.76 g).

Workup

  1. temperatureThe mixture was refluxed for 12 hrs
  2. customthe solvents were evaporated
  3. customPurification by flash chromatography
  4. washeluting with dichloromethane

Sources & evidence

ORD record
ord-a5057c5d45694d73a49d77ba26bb1865
Source dataset
uspto-grants-2009_04
Patent number
US07517989B2

Reaction notes

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