Hydrochloric Acid → 1-(p-Fluoroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

HRID 27156Notes

Reaction equation

HRID 27156 reaction equation
[ClH:1].C(OC([N:12]([CH2:20][CH:21]1[C:30]2[C:25](=[CH:26][C:27]([OH:32])=[C:28]([OH:31])[CH:29]=2)[CH2:24][CH2:23][NH:22]1)[C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)=O)C1C=CC=CC=1.Cl>C(O)(=O)C>[ClH:1].[F:19][C:16]1[CH:15]=[CH:14][C:13]([NH:12][CH2:20][CH:21]2[C:30]3[C:25](=[CH:26][C:27]([OH:32])=[C:28]([OH:31])[CH:29]=3)[CH2:24][CH2:23][NH:22]2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 204605421-(N-benzyloxycarbonyl-p-fluoroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 204605531-(p-Fluoroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochlorideYield 95.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1-(N-benzyloxycarbonyl-p-fluoroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (4.6 g), conc. hydrochloric acid (46 ml) and acetic acid (46 ml) was refluxed for 2 hours. The reaction mixture was concentrated to dryness and the residue was dissolved in water and washed with a mixture of ether and ethyl acetate (1:1). The aqueous layer was treated with activated charcoal and concentrated to dryness to give 1-(p-fluoroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (3.1 g). The product (2.5 g) was converted into its d-camphor-10-sulfonate in a conventional manner and the crystals obtained were recrystallized from water to give the d-camphor-10-sulfonate of the above-mentioned product, mp 213° to 215° C.

Workup

  1. temperaturewas refluxed for 2 hours
  2. concentrationThe reaction mixture was concentrated to dryness
  3. dissolutionthe residue was dissolved in water
  4. washwashed with a mixture of ether and ethyl acetate (1:1)
  5. additionThe aqueous layer was treated with activated charcoal
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-316e899e7fdd4442ac98f6af9ab9d26b
Source dataset
uspto-grants-1980_09
Patent number
US04220647

Reaction notes

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