Thionyl Chloride → HCID 67119973, compound

HRID 1888094Notes

Reaction equation

HRID 1888094 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.O=S(Cl)[Cl:29]>ClCCl>[ClH:29].[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)([Cl:29])[CH2:13][CH2:12]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 25167670HCID 25167670, compound2×

Product 1

HCID 67119973HCID 67119973, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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 in an ice-water bath with temperature controlled at below 0° C. The reaction solution is added dropwise a dichloromethane solution (8 mol, 25 ml) of SOCl2. After completion of addition, the temperature is raised to room temperature slowly and reacting for 1 hour. Then operating according to the post-treatment method in General Method seven obtains 0.65 g of a white crystal, with yield of 38.1%.

Workup

  1. customaccording to the method of synthesis
  2. temperaturecooled in an ice-water bath with temperature
  3. customcontrolled at below 0° C
  4. additionAfter completion of addition

Sources & evidence

ORD record
ord-c5bdf10dc8304b82891951ef0718cf75
Source dataset
uspto-grants-2013_08
Patent number
US08501778B2

Reaction notes

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