Sodium Iodide → HCID 20266431, compound

HRID 1719718Notes

Reaction equation

HRID 1719718 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][C:13]2([OH:33])[CH2:18][CH2:17][N:16]([C:19]3[C:28]4[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=4)[N:22]=[CH:21][N:20]=3)[CH2:15][CH2:14]2)(=O)=O)=CC=1.[I-:35].[Na+]>CC(=O)CC>[CH3:30][O:29][C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][C:25]=1[O:31][CH3:32])[N:22]=[CH:21][N:20]=[C:19]2[N:16]1[CH2:17][CH2:18][C:13]([OH:33])([CH2:12][CH2:11][I:35])[CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 20266413HCID 20266413, compound

Product 1

HCID 20266431HCID 20266431, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 1-[4-toluenesulphonyloxy]-2-[1-(6,7-dimethoxyquinazolin-4-yl)-4-hydroxy-piperid-4-yl]ethane (0.6 g) and sodium iodide (1.84 g) in butan-2-one (10 cm3) was heated under reflux for 2.5 hours. Volatile material was removed in vacuo and the residue partitioned between chloroform (20 cm3) and water (20 cm3). The dried (MgSO4) organic phase was evaporated and the residue was crystallized from ethyl acetate to afford 6,7-dimethoxy-4-[4-hydroxy-4-(2-iodoethyl)piperid-1-yl]quinazoline, m.p. 179°-181°, (0.3 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2.5 hours
  3. customVolatile material was removed in vacuo
  4. customthe residue partitioned between chloroform (20 cm3) and water (20 cm3)
  5. dry with materialThe dried (MgSO4) organic phase
  6. customwas evaporated
  7. customthe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-3031ef265db84e2ca1c864ebea6278c5
Source dataset
uspto-grants-1985_09
Patent number
US04542132

Reaction notes

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