Sodium hydride → HCID 20266386, compound

HRID 1719717Notes

Reaction equation

HRID 1719717 reaction equation
[H-].[Na+].C1(C)C=CC(S(O[CH2:13][C:14]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]3[C:32]4[C:27](=[CH:28][C:29]([O:35][CH3:36])=[C:30]([O:33][CH3:34])[CH:31]=4)[N:26]=[CH:25][N:24]=3)[CH2:19][CH2:18]2)([OH:16])[CH3:15])(=O)=O)=CC=1>C1COCC1>[CH3:15][C:14]1([CH:17]2[CH2:18][CH2:19][N:20]([C:23]3[C:32]4[C:27](=[CH:28][C:29]([O:35][CH3:36])=[C:30]([O:33][CH3:34])[CH:31]=4)[N:26]=[CH:25][N:24]=3)[CH2:21][CH2:22]2)[CH2:13][O:16]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 20266400HCID 20266400, compound

Product 1

HCID 20266386HCID 20266386, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (2.5 g of a 50% dispersion in oil) was added to a stirred suspension of 1-[4-toluenesulphonyloxy]-2-[1-(6,7-dimethoxyquinazolin-4-yl)piperid-4-yl]-2-hydroxypropane (8.6 g) in THF (20 cm3) and the mixture was heated under reflux for 16 hours. Volatile material was removed in vacuo, the residue was partitioned between chloroform (50 cm3) and water (50 cm3) and the aqueous phase was further extracted with chloroform (2×50 cm3). The combined, dried (MgSO4) organic phase was evaporated and the residue was crystallized from ethyl acetate to afford 2-methyl-2-[1-(6,7-dimethoxy-quinazolin-4-yl)piperid-4-yl]oxirane, m.p. 125°-127.5° (5.0 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 16 hours
  3. customVolatile material was removed in vacuo
  4. customthe residue was partitioned between chloroform (50 cm3) and water (50 cm3)
  5. extractionthe aqueous phase was further extracted with chloroform (2×50 cm3)
  6. dry with materialdried (MgSO4) organic phase
  7. customwas evaporated
  8. customthe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-1bed0d49fda7414780f3d8db6a0770f9
Source dataset
uspto-grants-1985_09
Patent number
US04542132

Reaction notes

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