Dimethyl Sulfoxide → HCID 19697611, compound

HRID 863226Notes

Reaction equation

HRID 863226 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH:10]([CH2:18][OH:19])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.CS(C)=O>C(N(CC)CC)C>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH:10]([CH:18]=[O:19])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 19697838HCID 19697838, compound

Product 1

HCID 19697611HCID 19697611, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

5.4 g of 1-benzyl-3(R,S)-hydroxymethyl-1,2,3,4-tetrahydroquinoline are reacted with 2.8 ml oxalyl chloride, 3.0 ml dimethylsulfoxide and 12 ml triethylamine analogously to Example 29b). Purification by means of FC is carried out over 500 g of silica gel (mobile phase D): Rf (D)=0.26; Rf (B)=0.41.

Workup

  1. customPurification by means of FC

Sources & evidence

ORD record
ord-48cea9ed139241e6945a562c45a5e285
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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