Hydrochloric Acid → 7-(4-(Trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride

HRID 1477229Notes

Reaction equation

HRID 1477229 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:18]=[C:17]3[C:12]([CH2:13][CH2:14][N:15](C(OC(C)(C)C)=O)[CH2:16]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[ClH:28].O1CCOCC1.C(OCC)C>C(Cl)Cl>[ClH:28].[F:27][C:2]([F:1])([F:26])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:18]=[C:17]3[C:12]([CH2:13][CH2:14][NH:15][CH2:16]3)=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 312751,4-DioxaneHCID 70974981tert-Butyl 7-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 709747087-(4-(Trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 7-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (1.4 g, 3.7 mmol) in DCM (3 mL) was added 4.0M HCl in dioxane (4.6 mL, 18.56 mmol) and stirred at rt for 3 h, Diethylether (200 mL) was then added and the mixture was stirred at rt for 30 min and then filtered and washed with diethylether and dried to give the title compound (1.3 grams).

Workup

  1. stirringthe mixture was stirred at rt for 30 min
  2. filtrationfiltered
  3. washwashed with diethylether
  4. customdried

Sources & evidence

ORD record
ord-31bbea5497a64d3abb73a3800f3d1115
Source dataset
uspto-grants-2016_08
Patent number
US09403782B2

Reaction notes

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