Chloroform → HCID 20266400, compound

HRID 1719716Notes

Reaction equation

HRID 1719716 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24][CH3:25])[N:20]=[CH:19][N:18]=[C:17]2[N:26]1[CH2:31][CH2:30][CH:29]([C:32]([OH:36])([CH3:35])[CH2:33][OH:34])[CH2:28][CH2:27]1.C(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:34][CH2:33][C:32]([OH:36])([CH:29]2[CH2:30][CH2:31][N:26]([C:17]3[C:16]4[C:21](=[CH:22][C:23]([O:24][CH3:25])=[C:14]([O:13][CH3:12])[CH:15]=4)[N:20]=[CH:19][N:18]=3)[CH2:27][CH2:28]2)[CH3:35])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 73974-Toluenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 20266401HCID 20266401, compound

Product 1

HCID 20266400HCID 20266400, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Toluene-4-sulphonylchloride (0.285 g) was added at 0° to a stirred solution of 2-[1-(6,7-dimethoxyquinazolin-4-yl)piperid-4-yl]propane-1,2-diol (0.35 g) in pyridine (3 cm3) and the mixture was stirred for 3 hours. The mixture was poured into a mixture of chloroform (20 cm3) and saturated sodium bicarbonate solution (20 cm3) and the dried (MgSO4) chloroform layer was evaporated. The residue was chromatographed on silica ("Merck" 60.9385) eluting with methanol:chloroform, 1:49, to give an oil which was crystallised from ethyl acetate to afford 1-[4-toluenesulphonyloxy]-2-hydroxy-2-[1-(6,7-dimethoxyquinazolin-4-yl)piperid-4-yl]propane, m.p. 120°-124° (0.285 g).

Workup

  1. dry with materialthe dried (MgSO4) chloroform layer
  2. customwas evaporated
  3. customThe residue was chromatographed on silica ("Merck" 60.9385)
  4. washeluting with methanol
  5. customchloroform, 1:49, to give an oil which
  6. customwas crystallised from ethyl acetate

Sources & evidence

ORD record
ord-14c19ffadf97407ca26cd8bcb3f388bc
Source dataset
uspto-grants-1985_09
Patent number
US04542132

Reaction notes

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