Dichloromethane → HCID 67119787, compound

HRID 1888089Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([N:11]2[CH2:16][CH2:15][C:14]([CH2:18][C:19](=[O:26])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(O)[CH2:13][CH2:12]2)[CH3:10])=[CH:5][CH:4]=1.C(=O)=O.CC(C)=O.CCN(S(F)(F)[F:40])CC.[Cl:43]CCl>>[ClH:43].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([N:11]2[CH2:16][CH2:15][C:14]([CH2:18][C:19](=[O:26])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([F:40])[CH2:13][CH2:12]2)[CH3:10])=[CH:5][CH:4]=1

Participants

Reactant 4

HCID 6344Dichloromethane2×

HCID 123472(Diethylamino)sulfur trifluoride

HCID 18522661Acetone cardice

HCID 25167673HCID 25167673, compound2×

Product 1

HCID 67119787HCID 67119787, compoundYield 34.8%

Conditions

Temperature: -75 °C

Procedure

N-(1-(4-methoxyphenyl)ethyl)-4-benzoylmethyl-4-piperidinol (III-19) is firstly prepared according to the method of synthesis and post-treatment in Example 19. 1.41 g (4.0 mmol) of N-(1-(4-methoxyphenyl)ethyl)-4-benzoylmethyl-4-piperidinol is taken and 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 protection 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 0.57 g of a white crystal, with yield of 34.8%.

Workup

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

Sources & evidence

ORD record: ord-791b3ceb356f4be3b0a85e04568f7b8f
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501778B2

Reaction notes

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