Dichloromethane → HCID 67119918, compound

HRID 1888092Notes

Reaction equation

HRID 1888092 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([CH:12]([N:14]3[CH2:19][CH2:18][C:17]([CH2:21][C:22](=[O:29])[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)(O)[CH2:16][CH2:15]3)[CH3:13])=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)=O.CC(C)=O.CCN(S(F)(F)[F:43])CC.[Cl:46]CCl>>[ClH:46].[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([CH:12]([N:14]3[CH2:19][CH2:18][C:17]([CH2:21][C:22](=[O:29])[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)([F:43])[CH2:16][CH2:15]3)[CH3:13])=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 123472(Diethylamino)sulfur trifluorideHCID 18522661Acetone cardiceHCID 25167803HCID 25167803, compound2×

Product 1

HCID 67119918HCID 67119918, compoundYield 40.2%

Conditions

Temperature
-75 °C

Procedure

N-(1-(4-(1-pyrrolidinyl)phenyl)ethyl)-4-benzoylmethyl-4-piperidinol (III-25) is firstly prepared according to the method of synthesis and post-treatment in Example 2. 1.57 g (4.0 mmol) of N-(1-(4-(1-pyrrolidinyl) 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 under 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 0.78 g of a white crystal, with yield of 40.2%.

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-5df910fac2f2499e8a19f96f90b8c9f4
Source dataset
uspto-grants-2013_08
Patent number
US08501778B2

Reaction notes

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