Acetic Acid → HCID 14620595, compound

HRID 231823Notes

Reaction equation

HRID 231823 reaction equation
Br.C(O)(=O)C.C[O:7][C:8]1[C:9]([O:27]C)=[CH:10][C:11]2[CH2:12][CH2:13][N:14]3[CH2:20][CH2:19][C:18]4[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=4[CH2:16][CH:15]3[C:25]=2[CH:26]=1>O1CCCC1>[CH:26]1[C:25]2[CH:15]3[CH2:16][C:17]4[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=4[CH2:19][CH2:20][N:14]3[CH2:13][CH2:12][C:11]=2[CH:10]=[C:9]([OH:27])[C:8]=1[OH:7]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 384200HCID 384200, compound

Product 1

HCID 14620595HCID 14620595, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Hydrobromic acid (48%, 30 ml) was added to a glacial acetic acid (3 ml) solution of 5,6,8,9,14,14a-hexahydro-2,3-dimethoxyisoquino[1,2-b][3]-benzazepine (XIIIc, Ex. 20) (0.928 g, 3 mmole), and the resulting solution was heated under reflux for 2.5 hours, then evaporated on a rotary evaporator to give a resinous residue. The residue was dissolved in tetrahydrofurane (about 80 ml), and the solution was allowed to sit at room temperature over a weekend. The crystalline product that was separated was collected on a filter, and washed with tetrahydrofurane to give the titled product which was recrystallized from ethanol. The product (HBr salt) weighed 0.8 g (73%) and melted at 270°-272°.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureunder reflux for 2.5 hours
  3. customevaporated on a rotary evaporator
  4. customto give a resinous residue
  5. waitto sit at room temperature over a weekend
  6. customThe crystalline product that was separated
  7. customwas collected on a filter
  8. washwashed with tetrahydrofurane

Sources & evidence

ORD record
ord-46bb8090f2454ff9b4a9d28de583517f
Source dataset
uspto-grants-1989_07
Patent number
US04849420

Reaction notes

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