Hydrochloric Acid → N-(5-(1-(4-(trifluoromethyl)phenyl)piperidin-4-yloxy)-2,3-dihydro-1H-inden-1-yl)piperidin-4-amine

HRID 705520Notes

Reaction equation

HRID 705520 reaction equation
[F:1][C:2]([F:40])([F:39])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([O:15][C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[CH:21]([NH:25][CH:26]3[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]3)[CH2:20][CH2:19]4)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.Cl>O1CCOCC1>[F:40][C:2]([F:1])([F:39])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([O:15][C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[CH:21]([NH:25][CH:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)[CH2:20][CH2:19]4)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57765814tert-butyl 4-(5-(1-(4-(trifluoromethyl)phenyl)piperidin-4-yloxy)-2,3-dihydro-1H-inden-1-ylamino)piperidine-1-carboxylate

Product 1

HCID 57765773N-(5-(1-(4-(trifluoromethyl)phenyl)piperidin-4-yloxy)-2,3-dihydro-1H-inden-1-yl)piperidin-4-amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of tert-butyl 4-(5-(1-(4-(trifluoromethyl)phenyl)piperidin-4-yloxy)-2,3-dihydro-1H-inden-1-ylamino)piperidine-1-carboxylate (0.73 g, 1.3 mmol) and 4N hydrochloric acid in dioxane (4 mL) was stirred at room temperature for 1 h. The reaction mixture was concentrated and washed with diethyl ether (2×5 mL) and then dried under reduced pressure to afford the title compound (as the 3.HCl salt) as a off-white solid (0.57 g, 97%). 1H NMR (CD3OD, 300 MHz) 7.73 (m, 2H), 7.58 (m, 3H), 7.07 (s, 1H), 7.01 (m, 1H), 4.93 (m, 1H), 4.78 (m, 1H), 3.65 (m, 6H), 3.20 (m, 5H), 2.62 (m, 1H), 2.35 (m, 6H), 2.08 (m, 5H) ppm; MS (ES) 460.7 (M+H)

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washwashed with diethyl ether (2×5 mL)
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-0fa3f7e1975e4dff91272e0a45b4d806
Source dataset
uspto-grants-2015_11
Patent number
US09174964B2

Reaction notes

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