Triethylamine → HCID 17960339, compound

HRID 456394Notes

Reaction equation

HRID 456394 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[CH2:19][CH2:18][O:17][CH:16]([CH2:20][OH:21])[CH2:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[N+:29]([C:32]1[CH:33]=[C:34]([S:38](Cl)(=[O:40])=[O:39])[CH:35]=[CH:36][CH:37]=1)([O-:31])=[O:30]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[CH2:19][CH2:18][O:17][CH:16]([CH2:20][O:21][S:38]([C:34]4[CH:35]=[CH:36][CH:37]=[C:32]([N+:29]([O-:31])=[O:30])[CH:33]=4)(=[O:39])=[O:40])[CH2:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 84763-Nitrobenzenesulfonyl chlorideHCID 17960331HCID 17960331, compound

Product 1

HCID 17960339HCID 17960339, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {4-[1-(4-chlorophenyl)-4-piperidinyl]-2-morpholinyl}methanol obtained from step (vi) (125 mg, 0.384 mmol) in dichloromethane (CH2Cl2) (2 mL) was added triethylamine (0.240 mL, 1.72 mmol) followed by 3-nitrobenzenesulfonyl chloride (127.5 mg, 0.575 mmol) and the reaction mixture kept on stirring at room temperature overnight. The volatiles were removed in vacuo, residue dissolved in chloroform, washed sucessively with saturated aqueous sodium hydrogen carbonate (NaHCO3) and water (H2O). The organic layer was dried over sodium sulphate (Na2SO4), filtered, concentrated and the residue was purified by silica gel flash chromatography to give the subtitled compound (163 mg).

Workup

  1. customThe volatiles were removed in vacuo, residue
  2. dissolutiondissolved in chloroform
  3. washwashed sucessively with saturated aqueous sodium hydrogen carbonate (NaHCO3) and water (H2O)
  4. dry with materialThe organic layer was dried over sodium sulphate (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-2f06d05ce8254231b3cd48becfa49515
Source dataset
uspto-grants-2007_03
Patent number
US07186718B2

Reaction notes

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