Diethyl Ether → 7-(4-(Trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride

HRID 517103

Reaction equation

HRID 517103 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.O1CCOCC1.C(OCC)C.C(Cl)[Cl:40]>>[ClH:40].[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

5

Reactant 4

HCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 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

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 was added 4.0M HO 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-4cefd45676d74f3f9c689da47a8482fb
Source dataset
uspto-grants-2015_08
Patent number
US09115096B2

Linked notes

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