Dichloromethane → HCID 67119774, compound

HRID 1888091Notes

Reaction equation

HRID 1888091 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([N:15]3[CH2:20][CH2:19][C:18]([CH2:22][C:23](=[O:30])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)(O)[CH2:17][CH2:16]3)[CH3:14])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C(=O)=O.CC(C)=O.CCN(S(F)(F)[F:44])CC.[Cl:47]CCl>>[ClH:47].[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([N:15]3[CH2:20][CH2:19][C:18]([CH2:22][C:23](=[O:30])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)([F:44])[CH2:17][CH2:16]3)[CH3:14])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 123472(Diethylamino)sulfur trifluorideHCID 18522661Acetone cardiceHCID 25167805HCID 25167805, compound2×

Product 1

HCID 67119774HCID 67119774, compoundYield 40.5%

Conditions

Temperature
-75 °C

Procedure

N-(1-(4-morpholinophenyl)ethyl)-4-benzoylmethyl-4-piperidinol (III-27) is firstly prepared according to the method of synthesis and post-treatment in Example 27. 1.63 g (4.0 mmol) of N-(1-(4-morpholino phenyl)ethyl)-4-benzoylmethyl-4-piperidinol is dissolved into 20 ml of anhydrous dichloromethane and cooled with dry ice-acetone with temperature controlled at below <−70° C. The reaction solution is added dropwise a dichloromethane solution (8 mol, 25 ml) of DAST protecting of nitrogen gas. After completion of addition, the temperature is maintained at −75° C. and reacting for 1 hour, and the temperature is raised slowly and maintained at −10° C. and reacting for 2 hours. Then operating according to the post-treatment method in General Method six obtains 0.81 g of a white crystal, with yield of 40.5%.

Workup

  1. customaccording to the method of synthesis
  2. customcontrolled at below <−70° C
  3. additionAfter completion of addition
  4. temperaturethe temperature is raised slowly
  5. temperaturemaintained at −10° C.
  6. waitreacting for 2 hours

Sources & evidence

ORD record
ord-1e59efeefece4e78b1f7f479a6714128
Source dataset
uspto-grants-2013_08
Patent number
US08501778B2

Reaction notes

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