Diethyl Ether → HCID 20389778, compound

HRID 426742Notes

Reaction equation

HRID 426742 reaction equation
[Cl:1][C:2]1[C:12]2[CH2:11][CH2:10][NH:9][CH2:8][CH:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[C:5]([Cl:19])=[C:4]([O:20][CH3:21])[C:3]=1[O:22][CH3:23].[OH-].[Na+].[CH3:26]COCC>C(O)=O.C=O>[Cl:1][C:2]1[C:12]2[CH2:11][CH2:10][N:9]([CH3:26])[CH2:8][CH:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[C:5]([Cl:19])=[C:4]([O:20][CH3:21])[C:3]=1[O:22][CH3:23]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 20389798HCID 20389798, compound

Product 1

HCID 20389778HCID 20389778, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 712FormaldehydeSolvent

Procedure

A mixture of 4 g of 6,9-dichloro-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine in 15 ml of formic acid and 10 ml of formaldehyde is refluxed for 18 hours. The mixture is evaporated in vacuo. The residue is treated with 20 ml of 6 N hydrochloric acid. The solution is again evaporated to give a residue which is treated with 20 ml of 10% sodium hydroxide solution then taken into ether. The ethereal extracts are dried and evaporated to give 6,9-dichloro-7,8-dimethoxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine.

Workup

  1. temperatureis refluxed for 18 hours
  2. customThe mixture is evaporated in vacuo
  3. additionThe residue is treated with 20 ml of 6 N hydrochloric acid
  4. customThe solution is again evaporated
  5. customto give a residue which
  6. customThe ethereal extracts are dried
  7. customevaporated

Sources & evidence

ORD record
ord-1a2238867b2e46a7ae772fd0024eb9aa
Source dataset
uspto-grants-1979_10
Patent number
US04171359

Reaction notes

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