Acetone → N-[2-(4-(2-Hydroxyethoxy)-phenyl)-1-methylethyl]-2-(6-chloro-pyridin-2-yl)-morpholine

HRID 1494312Notes

Reaction equation

HRID 1494312 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([N:14]2[C:19](=O)[CH2:18][O:17][CH:16]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[N:22]=3)[CH2:15]2)[CH3:13])=[CH:7][CH:6]=1.CC(C)=O>O1CCCC1.B.O1CCCC1>[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([N:14]2[CH2:19][CH2:18][O:17][CH:16]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[N:22]=3)[CH2:15]2)[CH3:13])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 180AcetoneHCID 14578858N-[2-(4-(2-Hydroxyethoxy)-phenyl)-1-methylethyl]-2-(6-chloro-pyridin-2-yl)-morpholin-5-one

Product 1

HCID 14578859N-[2-(4-(2-Hydroxyethoxy)-phenyl)-1-methylethyl]-2-(6-chloro-pyridin-2-yl)-morpholine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 2723981Borane;tetrahydrofuranSolvent

Procedure

0.7 g of N-[2-(4-(2-hydroxyethoxy)-phenyl)-1-methylethyl]-2-(6-chloro-pyridin-2-yl)-morpholin-5-one are dissolved in 20 ml of tetrahydrofuran and over a period of 3 hours at ambient temperature 3 times 4 ml of a 1 molar borane/tetrahydrofuran solution are added. Then 30 ml of acetone are added and the mixture is evaporated down. The residue is dissolved in 100 ml of methanol and stirred for 20 hours. The solvent is distilled off in vacuo and the residue is purified over a silica gel column with ethyl acetate as eluant.

Workup

  1. additionare added
  2. customthe mixture is evaporated down
  3. dissolutionThe residue is dissolved in 100 ml of methanol
  4. distillationThe solvent is distilled off in vacuo
  5. customthe residue is purified over a silica gel column with ethyl acetate as eluant

Sources & evidence

ORD record
ord-13cc385a9b754e6ebb0fcb5c7d46d581
Source dataset
uspto-grants-1991_06
Patent number
US05026702

Reaction notes

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