Benzene → HCID 70603370, compound

HRID 1606120Notes

Reaction equation

HRID 1606120 reaction equation
[CH3:1][C:2]1[C:12]2[CH2:11][CH2:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[C:7]([CH2:18][CH2:19][CH2:20][N:21](C)C)([OH:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:24]([O:26][C:27](Cl)=[O:28])[CH3:25].[CH:30]1C=CC=CC=1>>[CH3:1][C:2]1[C:12]2[CH2:11][CH2:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[C:7]([CH2:18][CH2:19][CH:20]([NH:21][C:27]([O:26][CH2:24][CH3:25])=[O:28])[CH3:30])([OH:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 241Benzene2×HCID 10928Ethyl chloroformateHCID 22750694HCID 22750694, compound

Product 1

HCID 70603370HCID 70603370, compound

Procedure

A solution containing 15.5 g. of 1-methyl-10,11-dihydro-5-(3-dimethylaminopropyl)-5-hydroxy-5-H-dibenzo[a,d]cycloheptene in 180 ml. of dry benzene is added dropwise to a mixture of 16.4 g. of chloroformic acid ethyl ester and 50 ml. of dry benzene and thereafter boiled at reflux for 20 hours. After cooling, the reaction mixture is washed with three 100 ml. portions of hydrochloric acid, then with water, dried over sodium sulfate and evaporated. The 1-methyl-10,11-dihydro-5-(3-methyl-carbethoxyaminopropyl)-5-hydroxy-5H-dibenzo[a,d]cycloheptene obtained is recrystallized from high-boiling petroleum ether and has a melting point of 132°-134° C.

Workup

  1. additionA solution containing 15.5 g
  2. temperatureat reflux for 20 hours
  3. temperatureAfter cooling
  4. washthe reaction mixture is washed with three 100 ml
  5. dry with materialportions of hydrochloric acid, then with water, dried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-ad4d15bd4ab6475eb3e94935b8b10893
Source dataset
uspto-grants-1976_04
Patent number
US03952017

Reaction notes

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