Diethyl Ether → HCID 22750664, compound

HRID 1606131Notes

Reaction equation

HRID 1606131 reaction equation
CCOCC.[CH3:6][N:7]([CH2:9][CH2:10][CH2:11]Cl)[CH3:8].[CH3:13][C:14]1([C:19]2[C:29]3[CH2:28][CH2:27][C:26]4[CH:30]=[CH:31][CH:32]=[CH:33][C:25]=4[C:24](=[O:34])[C:23]=3[CH:22]=[CH:21][CH:20]=2)[O:18][CH2:17][CH2:16][O:15]1>O1CCCC1>[CH3:13][C:14]1([C:19]2[C:29]3[CH2:28][CH2:27][C:26]4[CH:30]=[CH:31][CH:32]=[CH:33][C:25]=4[C:24]([CH2:11][CH2:10][CH2:9][N:7]([CH3:8])[CH3:6])([OH:34])[C:23]=3[CH:22]=[CH:21][CH:20]=2)[O:15][CH2:16][CH2:17][O:18]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 22750660HCID 22750660, compound

Product 1

HCID 22750664HCID 22750664, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Utilizing 1.13 g. of Gilman alloy, 5 ml. of absolute ether, 5.2 g. of dimethylaminoproyl chloride and 5 ml. of absolute tetrahydrofuran, in a similar manner, is obtained the corresponding Grignard compound. After cooling to 0°C., there is added dropwise a solution containing 7.2 g. of 1-(2-methyl-1,3-dioxolan-2-yl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one in 40 ml. of absolute tetrahydrofuran. Subsequently, the mixture is heated for 3 hours at reflux, cooled to about 0°C., hydrolyzed with 4 ml. of water, filtered, and then washed with ether. The ethereal solution is dried over sodium sulfate, filtered and concentrated under reduced pressure, whereby 1-(2-methyl-1,3-dioxolan-2-yl)-10,11-dihydro-5-(3-dimethylaminopropyl)-5-hydroxy-5H-dibenzo[a,d]cycloheptene is obtained as a yellow oil which is crystallized from 50 ml. of high-boiling petroleum ether and has a melting point of 122°-124°C.

Workup

  1. additionthere is added dropwise a solution
  2. additioncontaining 7.2 g
  3. temperatureSubsequently, the mixture is heated for 3 hours
  4. temperatureat reflux
  5. temperaturecooled to about 0°C., hydrolyzed with 4 ml
  6. filtrationof water, filtered
  7. washwashed with ether
  8. dry with materialThe ethereal solution is dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9290fe0f006b413698164d66b9db1d5d
Source dataset
uspto-grants-1976_04
Patent number
US03952017

Reaction notes

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