Hydrochloric Acid → n-(Piperidin-4-yl)-6-(1-(4-(trifluoromethyl)phenyl)piperidin-4-yloxy)benzo[d]oxazole-2-carboxamide dihydrochloride salt

HRID 1773450Notes

Reaction equation

HRID 1773450 reaction equation
[F:1][C:2]([F:42])([F:41])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([O:15][C:16]3[CH:40]=[CH:39][C:19]4[N:20]=[C:21]([C:23]([NH:25][CH:26]5[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]5)=[O:24])[O:22][C:18]=4[CH:17]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[ClH:43]>O1CCOCC1>[ClH:43].[ClH:43].[NH:29]1[CH2:30][CH2:31][CH:26]([NH:25][C:23]([C:21]2[O:22][C:18]3[CH:17]=[C:16]([O:15][CH:12]4[CH2:11][CH2:10][N:9]([C:6]5[CH:5]=[CH:4][C:3]([C:2]([F:42])([F:1])[F:41])=[CH:8][CH:7]=5)[CH2:14][CH2:13]4)[CH:40]=[CH:39][C:19]=3[N:20]=2)=[O:24])[CH2:27][CH2:28]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57951056Tert-butyl 4-(6-(1-(4-(trifluoromethyl)phenyl)piperidin-4-yloxy)benzo[d]oxazole-2-carboxamido)piperidine-1-carboxylate2×

Product 1

HCID 66899850n-(Piperidin-4-yl)-6-(1-(4-(trifluoromethyl)phenyl)piperidin-4-yloxy)benzo[d]oxazole-2-carboxamide dihydrochloride saltYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of tert-butyl 4-(6-(1-(4-(trifluoromethyl)phenyl)piperidin-4-yloxy)benzo[d]oxazole-2-carboxamido)piperidine-1-carboxylate (compound 1) (0.16 g, 0.27 mmol) and 4N hydrochloric acid in dioxane (2 mL) was stirred at room temperature for 1 h. The reaction mixture was concentrated and washed with diethyl ether (2×3 mL) and then dried under reduced pressure to afford N-(piperidin-4-yl)-6-(1-(4-(trifluoromethyl)phenyl)piperidin-4-yloxy)benzo[d]oxazole-2-carboxamide dihydrochloride salt as a off-white solid (0.15 g, 99%). 1H NMR (CD3OD, 300 MHz) 7.83 (m, 5H), 7.48 (s, 1H), 7.23 (m, 1H), 4.93 (m, 1H), 4.22 (m, 1H), 3.90 (m, 3H), 3.35 (m, 2H), 3.17 (m, 2H), 2.23 (m, 8H), 1.98 (m, 2H) ppm; MS (ES) 489.1 (M+1).

Workup

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

Sources & evidence

ORD record
ord-0312208ba4804453b5ec542b5cbcd1a8
Source dataset
uspto-grants-2016_02
Patent number
US09255085B2

Reaction notes

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