Water → 5-(4-isopropylmorpholin-2-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

HRID 2083374Notes

Reaction equation

HRID 2083374 reaction equation
C([Li])CCC.[CH:6]1[C:16]2[CH2:15][CH2:14][C:13]3[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=3[CH2:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.Cl[CH2:22][CH:23]1[O:28][CH2:27][CH2:26][N:25]([CH:29]([CH3:31])[CH3:30])[CH2:24]1.O>CCCCCC.O1CCCC1.C1C=CC=CC=1>[CH:29]([N:25]1[CH2:26][CH2:27][O:28][CH:23]([CH2:22][CH:11]2[C:12]3[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=3[CH2:14][CH2:15][C:16]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]2=3)[CH2:24]1)([CH3:31])[CH3:30]

Participants

8

Reactant 4

HCID 962WaterHCID 7002910,11-dihydro-5H-dibenzo(a,d)cyclohepteneHCID 128324802-(Chloromethyl)-4-(propan-2-yl)morpholineHCID 178418339Butyllithium

Product 1

HCID 128324815-(4-isopropylmorpholin-2-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of n-butyl lithium in n-hexane (1.6 N, 1.6 ml) was added to 10,11-dihydro-5H-dibenzo[a,d]cycloheptene (390 mg) in anhydrous tetrahydrofuran at room temperature, and the resulting mixture was stirred under reflux for 40 minutes. A solution of 2-chloromethyl-4-isopropylmorpholine (362 mg) in benzene was added thereto while stirring under heating, and the resulting mixture was stirred under reflux for 4 hours, followed by addition of excess water. The reaction mixture was extracted with ethyl acetate. The ethyl acetate extract was dried, evaporated and chromatographed to afford 5-(4-isopropylmorpholin-2-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cycloheptene as oily material. M.P., 219° - 221° C (hydrochloride).

Workup

  1. temperatureunder reflux for 40 minutes
  2. stirringwhile stirring
  3. temperatureunder heating
  4. stirringthe resulting mixture was stirred
  5. temperatureunder reflux for 4 hours
  6. extractionThe reaction mixture was extracted with ethyl acetate
  7. extractionThe ethyl acetate extract
  8. customwas dried
  9. customevaporated
  10. customchromatographed

Sources & evidence

ORD record
ord-f23ede89ffda4f6488634d59163d47a1
Source dataset
uspto-grants-1978_04
Patent number
US04085210

Reaction notes

Loading…