N,N-Dimethyl-1,3-propanediamine → HCID 23456459, compound

HRID 1973469Notes

Reaction equation

HRID 1973469 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]([C:6](=O)[CH2:7][CH:8]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]2=O)=[CH:4][CH:3]=1.[CH3:19][N:20]([CH2:22][CH2:23][CH2:24][NH2:25])[CH3:21]>Cl.C(O)C>[CH3:19][N:20]([CH3:21])[CH2:22][CH2:23][CH2:24][N:25]1[C:6]([C:5]2[CH:17]=[CH:18][C:2]([Br:1])=[CH:3][CH:4]=2)=[CH:7][C:8]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=2

Participants

5

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 214915222-[2-(4-Bromophenyl)-2-oxoethyl]cycloheptan-1-one

Product 1

HCID 23456459HCID 23456459, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

A mixture of 18.6 (0.06 mole) of 2-(p-bromophenacyl)cycloheptanone and 6.19 g (0.06 mole) of dimethylaminopropylamine is dissolved in 200 ml. of absolute ethanol. A few drops of concentrated hydrochloric acid are added and the mixture is refluxed for 4 hours. The ethanol is evaporated, and the residue is dissolved in dilute hydrochloric acid and washed with ether. The aqueous solution is basified with sodium carbonate solution and extracted with ether. The ether solution is washed with water, dried, and concentrated to a brown oil which solidifies upon cooling. The resulting solid is recrystallized from petroleum ether to give 1-(3-dimethylaminopropyl)-2-(p-bromophenyl)-1,4,5,6,7,8-hexahydrocyclohepta[b]pyrrole, m.p. 69°-70° C.

Workup

  1. dissolutionis dissolved in 200 ml
  2. temperaturethe mixture is refluxed for 4 hours
  3. customThe ethanol is evaporated
  4. dissolutionthe residue is dissolved in dilute hydrochloric acid
  5. washwashed with ether
  6. extractionextracted with ether
  7. washThe ether solution is washed with water
  8. customdried
  9. concentrationconcentrated to a brown oil which
  10. temperatureupon cooling
  11. customThe resulting solid is recrystallized from petroleum ether

Sources & evidence

ORD record
ord-dee617194f9c49b1bb777e1555fb3ab8
Source dataset
uspto-grants-1976_12
Patent number
US03997557

Reaction notes

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