Dichloromethane → HCID 67119786, compound

HRID 1888090Notes

Reaction equation

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

Participants

Reactant 4

HCID 6344Dichloromethane2×

HCID 123472(Diethylamino)sulfur trifluoride

HCID 18522661Acetone cardice

HCID 25167670HCID 25167670, compound2×

Product 1

HCID 67119786HCID 67119786, compoundYield 37.2%

Conditions

Temperature: -75 °C

Procedure

N-(benzo[d][1,3]dioxol-5-ylmethyl)-4-benzoylmethyl-4-piperidinol (III-13) is firstly prepared according to the method of synthesis and post-treatment in Example 13. 1.41 g (4.0 mmol) of N-(benzo[d][1,3]dioxol-5-ylmethyl)-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 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 0.61 g of a white crystal, with yield of 37.2%.

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-0ac90bb2c0714fd08fb85240db3a20b4
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501778B2

Reaction notes

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