Hydrochloric Acid → 6-(4-Amino-benzylamino)-7-chloro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]-azepine Hydrochloride

HRID 1191035Notes

Reaction equation

HRID 1191035 reaction equation
Cl.O1CCOCC1.C(OC([NH:15][C:16]1[CH:41]=[CH:40][C:19]([CH2:20][NH:21][C:22]2[C:32]3[CH2:31][CH2:30][N:29]([C:33](=[O:38])[C:34]([F:37])([F:36])[F:35])[CH2:28][CH2:27][C:26]=3[CH:25]=[CH:24][C:23]=2[Cl:39])=[CH:18][CH:17]=1)=O)(C)(C)C.C(OCC)C>O1CCOCC1.C(Cl)Cl>[ClH:39].[NH2:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:20][NH:21][C:22]2[C:32]3[CH2:31][CH2:30][N:29]([C:33](=[O:38])[C:34]([F:37])([F:35])[F:36])[CH2:28][CH2:27][C:26]=3[CH:25]=[CH:24][C:23]=2[Cl:39])=[CH:40][CH:41]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 312751,4-DioxaneHCID 584956276-(4-tert-butoxycarbonylamino-benzylamino)-7-chloro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]-azepine

Product 1

HCID 866241586-(4-Amino-benzylamino)-7-chloro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]-azepine HydrochlorideYield 229.2%

Reagents, catalysts & solvents 1

HCID 18626912Dioxane methylene chlorideSolvent

Procedure

Add 4M hydrogen chloride in dioxane (20 mL, 20 mmol) to a solution of 6-(4-tert-butoxycarbonylamino-benzylamino)-7-chloro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]-azepine (0.219, 0.44 mmol) in 1,4-dioxane/DCM (1:1, 40 mL). Stir overnight at room temperature, add diethyl ether and concentrate in vacuo to obtain the title compound (0.219 g, 100%) that was dried in vacuo.

Workup

  1. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-d6caa4922e9949759fed2a1ef05c90e8
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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