4-(3,4-Dichlorophenoxy)piperidine → Ammonia

HRID 1292754Notes

Reaction equation

HRID 1292754 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][CH:22]1[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 57791474Tert-butyl 2-(((methylsulfonyl)oxy)methyl)morpholine-4-carboxylate

Product 2

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the product from Example 1, Step (b) dissolved in acetonitrile (12 ml) was added the product of Example 2, Step (a). The mixture was refluxed for 12 hrs and the solvents were evaporated. Purification by flash chromatography (silica) eluting with dichloromethane: methanol: NH3 (aq) (2:98:0.1) gave the sub-title compound as an oil (1.9 g).

Workup

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

Sources & evidence

ORD record
ord-035fcec48b814741adcef02eb7c64b74
Source dataset
uspto-grants-2007_07
Patent number
US07238691B2

Reaction notes

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