Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester → HCID 22750661, compound

HRID 1606119Notes

Reaction equation

HRID 1606119 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](=[CH:17][CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])[C:6]=2[CH:5]=[CH:4][CH:3]=1.CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>[Pt]=O>[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]([CH3:22])[CH3:21])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 53836108HCID 53836108, compound

Product 1

HCID 22750661HCID 22750661, compound

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

Procedure

39.5 g. of 1-methyl-10,11-dihydro-5-(3-dimethylaminopropylidene)-5H-dibenzo[a,d]cycloheptene are dissolved in 400 ml. of glacial acetic and hydrogenated at room temperature and under normal pressure in the presence of 3 g. of platinum oxide. When the uptake of hydrogen ceases, the catalyst is removed by filtration. The filtrate is evaporated, and the residue distilled whereby 1-methyl-10,11-dihydro-5-(3-dimethylaminopropyl)-5H-dibenzo[a,d]cycloheptene goes over at 140° C. under 0.01 mmHg. The corresponding hydrochloride salt has a melting point of 181°-183° C. after recrystallization from ethanol-ether.

Workup

  1. customhydrogenated at room temperature
  2. customWhen the uptake of hydrogen ceases, the catalyst is removed by filtration
  3. customThe filtrate is evaporated
  4. distillationthe residue distilled whereby 1-methyl-10,11-dihydro-5-(3-dimethylaminopropyl)-5H-dibenzo[a,d]cycloheptene
  5. customgoes over at 140° C. under 0.01 mmHg
  6. customafter recrystallization from ethanol-ether

Sources & evidence

ORD record
ord-9a037fab42be42e493168e551d704304
Source dataset
uspto-grants-1976_04
Patent number
US03952017

Reaction notes

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