Allyl bromide → 1-[2-(N-isopropyl-N-allylamino)propyl]-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one

HRID 1105551Notes

Reaction equation

HRID 1105551 reaction equation
Cl.[CH:2]([NH:5][CH:6]([CH3:26])[CH2:7][C:8]1[C:9](=[O:25])[NH:10][CH2:11][CH2:12][CH:13]2[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:23][CH3:24])[CH:19]=3)[C:14]=12)([CH3:4])[CH3:3].[CH2:27](Br)[CH:28]=[CH2:29].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH:2]([N:5]([CH:6]([CH3:26])[CH2:7][C:8]1[C:9](=[O:25])[NH:10][CH2:11][CH2:12][CH:13]2[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:23][CH3:24])[CH:19]=3)[C:14]=12)[CH2:29][CH:28]=[CH2:27])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 7841Allyl bromide2×HCID 11430Potassium Carbonate2×HCID 205555941-(2-isopropylaminopropyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one hydrochloride

Product 1

HCID 128324191-[2-(N-isopropyl-N-allylamino)propyl]-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 7.58 g of slow moving 1-(2-isopropylaminopropyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one hydrochloride, 4.8 g of allyl bromide, 5.5 g of potassium carbonate and 100 ml of anhydrous ethanol is refluxed for 3 hours. The mixture is recharged with 2.4 g of allyl bromide and 2.75 g of potassium carbonate and refluxed overnight. It is evaporated, water is added to the residue and the mixture extracted with chloroform. The extract is evaporated, the residue crystallized from petroleum ether and recrystallized from ethyl acetate to yield the 1-[2-(N-isopropyl-N-allylamino)propyl]-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one, melting at 168°-170°.

Workup

  1. additionThe mixture of 7.58 g
  2. temperatureis refluxed for 3 hours
  3. temperaturerefluxed overnight
  4. customIt is evaporated
  5. additionwater is added to the residue
  6. extractionthe mixture extracted with chloroform
  7. customThe extract is evaporated
  8. customthe residue crystallized from petroleum ether
  9. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-0bb98a3a61f4498b8af64923269f27b0
Source dataset
uspto-grants-1982_01
Patent number
US04309345

Reaction notes

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