Water → 1,10-dimethyl-3,4-dihydro-1H-1,4-oxazino[4,3-a]indole 1-propyl tosylate

HRID 1657751

Reaction equation

HRID 1657751 reaction equation
[CH3:1][C:2]1(CCCO)[C:7]2=[C:8]([CH3:15])[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[N:6]2[CH2:5][CH2:4][O:3]1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.O>N1C=CC=CC=1>[CH3:1][CH:2]1[C:7]2=[C:8]([CH3:15])[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[N:6]2[CH2:5][CH2:4][O:3]1.[S:26]([C:23]1[CH:24]=[CH:25][C:20]([CH3:30])=[CH:21][CH:22]=1)([O:3][CH2:2][CH2:7][CH3:8])(=[O:28])=[O:27]

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 213895531,10-Dimethyl-3,4-dihydro-1H-1,4-oxazino[4,3-a]indole-1-propanol

Product 1

HCID 867335231,10-dimethyl-3,4-dihydro-1H-1,4-oxazino[4,3-a]indole 1-propyl tosylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1,10-Dimethyl-3,4-dihydro-1H-1,4-oxazino[4,3-a]indole-1-propanol (9.5 g.), described in Example 462, is dissolved in dry pyridine (20 ml.). p-Toluenesulfonyl chloride (7.4 g.) is added portionwise to the vigorously stirred and cooled solution. The mixture is stirred further at 0°C. for 1 hr., ice and water is then added and the aqueous mixture is extracted with ether. The combined ether extracts are washed with 10% ice-cold hydrochloric acid, water, 5% sodium bicarbonate water and dried (Na2SO4). Concentration of the extracts affords 1,10-dimethyl-3,4-dihydro-1H-1,4-oxazino[4,3-a]indole-1-propyl tosylate, δCHCl3max 1600, 1370, 1190 and 1170 cm-1.

Workup

  1. temperaturecooled solution
  2. stirringThe mixture is stirred further at 0°C. for 1 hr
  3. extractionthe aqueous mixture is extracted with ether
  4. washThe combined ether extracts are washed with 10% ice-cold hydrochloric acid, water, 5% sodium bicarbonate water
  5. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-be66594db2fa428c91ecf9a2d8d61c67
Source dataset
uspto-grants-1976_06
Patent number
US03962236

Linked notes

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