Acetone → HCID 21412124, compound

HRID 1284233Notes

Reaction equation

HRID 1284233 reaction equation
[H][H].[NH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH:11]=[CH:10][C:9]2[CH:18]=[CH:19][CH:20]=[CH:21][C:8]1=2.[CH3:22][C:23]([CH3:25])=O>[Pt]=O>[CH:23]([NH:3][CH2:4][CH2:5][CH2:6][CH:7]1[C:8]2[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=2[CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]1=2)([CH3:25])[CH3:22]

Participants

5

Reactant 3

HCID 180AcetoneHCID 214120995H-Dibenzo[a,d]cycloheptene-5-propanamineHCID 178418361HCID 178418361, compound3×

Product 1

HCID 21412124HCID 21412124, compound

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

Procedure

A suspension of platinum oxide (20 mg.) in 2 ml. of absolute alcohol is pre-reduced by shaking with hydrogen in a Hershberg apparatus. A solution of 5-(3-aminopropyl)-5H-dibenzo[a,d]cycloheptene (0.75 g., 0.003 mole) and acetone (0.5 ml.) in 5 ml. of absolute alcohol is added and the mixture shaken with hydrogen in a Hershberg apparatus until the hydrogen uptake is complete. Catalyst is filtered through a mat of diatomaceous earth and washed with absolute alcohol. The combined filtrate and washings are evaporated to dryness on the steam-bath under reduced pressure. The residual oily base is dissolved in absolute alcohol and treated with a solution of dry hydrogen chloride in absolute alcohol. The white crystalline 5-(3-isopropylaminopropyl)-5H-dibenzo[a,d]cycloheptene hydrochloride is precipitated by addition of absolute ether in a yield of 0.80 g. (92%), m.p. 234°-236°C. The melting point was unchanged by a further recrystallization from a mixture of isopropyl alcohol and absolute ether.

Workup

  1. filtrationCatalyst is filtered through a mat of diatomaceous earth
  2. washwashed with absolute alcohol
  3. customThe combined filtrate and washings are evaporated to dryness on the steam-bath under reduced pressure
  4. dissolutionThe residual oily base is dissolved in absolute alcohol
  5. additiontreated with a solution of dry hydrogen chloride in absolute alcohol
  6. customThe white crystalline 5-(3-isopropylaminopropyl)-5H-dibenzo[a,d]cycloheptene hydrochloride is precipitated by addition of absolute ether in a yield of 0.80 g
  7. customThe melting point was unchanged by a further recrystallization from a mixture of isopropyl alcohol and absolute ether

Sources & evidence

ORD record
ord-b4453fb5806942d6bebb67aacd49ff32
Source dataset
uspto-grants-1976_08
Patent number
US03978121

Reaction notes

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