Hydrochloric Acid → 6-Phenethyl-7-(trifluoromethyl)-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indole

HRID 1505720Notes

Reaction equation

HRID 1505720 reaction equation
[CH2:1]([C:9]1[C:10]([C:29]([F:32])([F:31])[F:30])=[C:11]2[C:15]3=[C:16]([CH2:18][NH:19][CH:20](C(OC(C)(C)C)=O)[CH2:21][N:14]3[CH:13]=[CH:12]2)[CH:17]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.O1CCOCC1>C(Cl)Cl>[CH2:1]([C:9]1[C:10]([C:29]([F:32])([F:31])[F:30])=[C:11]2[C:15]3=[C:16]([CH2:18][NH:19][CH2:20][CH2:21][N:14]3[CH:13]=[CH:12]2)[CH:17]=1)[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86691986tert-butyl 6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indole-2(1H)-carboxylate

Product 1

HCID 866919886-Phenethyl-7-(trifluoromethyl)-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indoleYield 103%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indole-2(1H)-carboxylate (1.4 g; 3.1 mmol) in CH2Cl2 at 0° C. was added 4M HCl in 1,4-dioxane (3.8 mL, 15.4 mmol). The resulting solution was warmed to room temperature and stirred overnight. The solid was collected to yield 6-phenethyl-7-(trifluoromethyl)-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indole (1.1 g).

Workup

  1. customThe solid was collected

Sources & evidence

ORD record
ord-e5bb9366c19e4411be00b9354f5a2dc0
Source dataset
uspto-grants-2015_12
Patent number
US09216998B2

Reaction notes

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