Ethyl chloroformate → HCID 22750666, compound

HRID 1606122Notes

Reaction equation

HRID 1606122 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[CH:7]([CH2:17][CH2:18][CH2:19][N:20](C)[CH3:21])[C:6]=2[CH:5]=[CH:4][CH:3]=1.ClC(OCC)=O>C1C=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[CH:7]([CH2:17][CH2:18][CH2:19][NH:20][CH3:21])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 22750661HCID 22750661, compound

Product 1

HCID 22750666HCID 22750666, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

12.2 g. of 1-methyl-10,11-dihydro-5-(3-dimethylaminopropyl)-5H-dibenzo[a,d]cycloheptene, dissolved in 180 ml. of dry benzene, are added dropwise to a mixture of 13.6 g. of ethyl chloroformate and 50 ml. of dry benzene. The mixture is boiled and stirred under reflux for 20 hours. After cooling, the benzene solution is washed with dilute hydrochloric acid and water and evaporated. The residual 1-methyl-10,11-dihydro-5-(3-methylcarbethoxyaminopropyl)-5H-dibenzo[a,d]cycloheptene distils at 180° C/0.01 mmHg. 10.6 g. of 1-methyl-10,11-dihydro-5-(3-methylcarbethoxyaminopropyl)-5H-dibenzo[a,d]cycloheptene, 12.6 g. of potassium hydroxide and 110 ml. of n-butanol are boiled at reflux for 20 hours under an atmosphere of nitrogen with strong stirring. The butanol is removed by distillation under reduced pressure. The residue is taken up in ether and the etheral solution shaken with dilute hydrochloric acid. By treatment of the aqueous acidic phase with excess potassium carbonate, 1-methyl-10,11-dihydro-5-(3-methylaminopropyl)-5H-dibenzo[a,d]cycloheptene separates out as an oil which distils at 150° C. under 0.01 mmHg. After recrystallization from ethanol-ether, the hydrochloride has a melting point of 173°-175° C.

Workup

  1. temperatureunder reflux for 20 hours
  2. temperatureAfter cooling
  3. washthe benzene solution is washed with dilute hydrochloric acid and water
  4. customevaporated
  5. customThe residual 1-methyl-10,11-dihydro-5-(3-methylcarbethoxyaminopropyl)-5H-dibenzo[a,d]cycloheptene distils at 180° C/0.01 mmHg
  6. temperatureat reflux for 20 hours under an atmosphere of nitrogen with strong stirring
  7. customThe butanol is removed by distillation under reduced pressure
  8. stirringthe etheral solution shaken with dilute hydrochloric acid
  9. customdistils at 150° C. under 0.01 mmHg
  10. customAfter recrystallization from ethanol-ether

Sources & evidence

ORD record
ord-eb9505ff162649e784391007e025fe90
Source dataset
uspto-grants-1976_04
Patent number
US03952017

Reaction notes

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