Hydrochloric Acid → Ammonium Hydroxide

HRID 2289305Notes

Reaction equation

HRID 2289305 reaction equation
C([O:5]C([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C:22]([N:24]3[CH2:29][CH2:28][CH:27]([N:30]4[C:35]5[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=5[CH2:33][O:32][C:31]4=[O:40])[CH2:26][CH2:25]3)=[O:23])=[C:17]([O:41][CH2:42][C:43]([F:46])([F:45])[F:44])[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>CCOC(C)=O>[NH:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C:22]([N:24]3[CH2:29][CH2:28][CH:27]([N:30]4[C:35]5[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=5[CH2:33][O:32][C:31]4=[O:40])[CH2:26][CH2:25]3)=[O:23])=[C:17]([O:41][CH2:42][C:43]([F:46])([F:44])[F:45])[CH:16]=2)[CH2:12][CH2:13]1.[NH4+:8].[OH-:5]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 9961083HCID 9961083, compound

Product 2

HCID 14923Ammonium HydroxideHCID 15840420HCID 15840420, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Into a stirred solution of 1-(1-(4-(N-tert-butyloxycarbonyl-4-piperidinyloxy)-2-(2,2,2-trifluoroethoxy)phenylacetyl)piperidin-4-yl)-4H-3,1-benzoxazin-2(1H)-one (0.55 g, 0.83 mmol) from Step 8 above in EtOAc (50 mL) at 0° C. was bubbled HCl gas for 15 min. The resulting suspension was stirred at 0° C. for 45 min. Excess HCl was removed by bubbling argon though the mixture for 15 min. Ether (50 mL) was added and the cold suspension was filtered. The solids were washed with additional ether and then dried under reduced pressure for 18 h to give the hydrochloride salt of 1-(1-(4-(4-piperidinyloxy)-2-(2,2,2-trifluoroethoxy)phenylacetyl)piperidin-4-yl)-4H-3,1-benzoxazin-2(1H)-one as an amorphous white powder (HPLC retention time=8.2 min (method B); TLC Rf =0.14 (90:10:0.5 CH2Cl2 :MeOH:NH4OH)).

Workup

  1. customExcess HCl was removed
  2. customby bubbling argon though the mixture for 15 min
  3. additionEther (50 mL) was added
  4. filtrationthe cold suspension was filtered
  5. washThe solids were washed with additional ether
  6. customdried under reduced pressure for 18 h

Sources & evidence

ORD record
ord-18f9456e9daf40ebbfaca19bc9c99114
Source dataset
uspto-grants-2000_07
Patent number
US06090805

Reaction notes

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