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

HRID 1105552
Notes
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Reaction equation

HRID 1105552 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].C(=O)([O-])[O-].[K+].[K+].[CH2:33](Br)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>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)[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([CH3:3])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7498Benzyl 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 128324231-[2-(N-isopropyl-N-benzylamino)-propyl]-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Procedure

To the solution of 5.0 g of the slow moving 1-(2-isopropylaminopropyl)-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one hydrochloride in 66 ml of anhydrous ethanol are added 3.64 g of anhydrous potassium carbonate and 3.14 ml of benzyl bromide. The mixture is refluxed for 3 hours while stirring and half of the original quantities of potassium carbonate and benzyl bromide are added. Refluxing is continued overnight and a second addition of the same reagents and refluxing for an additional day leads to complete benzylation. The mixture is evaporated, the residue diluted with water, extracted with chloroform and the extract dried and evaporated. The crude product is crystallized from petroleum ether and recrystallized from ethanol to give the 1-[2-(N-isopropyl-N-benzylamino)-propyl]-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepin-2-one, melting at 205°-207°.

Workup

  1. temperatureThe mixture is refluxed for 3 hours
  2. temperatureRefluxing
  3. additiona second addition of the same reagents
  4. temperaturerefluxing for an additional day
  5. customThe mixture is evaporated
  6. additionthe residue diluted with water
  7. extractionextracted with chloroform
  8. customthe extract dried
  9. customevaporated
  10. customThe crude product is crystallized from petroleum ether
  11. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-7a2cf6fbed8a42a5853a0b54dcf88ee2
Source dataset
uspto-grants-1982_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04309345

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes