Hydrochloric Acid → Ammonium Hydroxide

HRID 2289304Notes

Reaction equation

HRID 2289304 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]=[C:39]([F:40])[C:34]=5[CH2:33][O:32][C:31]4=[O:41])[CH2:26][CH2:25]3)=[O:23])=[C:17]([O:42][CH2:43][C:44]([F:47])([F:46])[F:45])[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[CH2:25][CH2:26][CH:27]([N:30]4[C:35]5[CH:36]=[CH:37][CH:38]=[C:39]([F:40])[C:34]=5[CH2:33][O:32][C:31]4=[O:41])[CH2:28][CH2:29]3)=[O:23])=[C:17]([O:42][CH2:43][C:44]([F:46])([F:47])[F:45])[CH:16]=2)[CH2:12][CH2:13]1.[NH4+:8].[OH-:5]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18700115HCID 18700115, compound

Product 2

HCID 14923Ammonium HydroxideHCID 18700093HCID 18700093, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Into a stirred solution of 1-(1-(4-(1-tert-butyloxycarbonyl-4-piperidinyloxy)-2-(2,2,2-trifluoroethoxy)phenyl-acetyl)piperidin-4-yl)-5-fluoro-4H-3,1-benzoxazin-2(1H)-one (0.35 g, 0.53 mmol) from Step 4 above in EtOAc (125 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 (125 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 of 1-(1-(4-(4-piperidinyloxy)-2-(2,2,2-trifluoroethoxy)phenylacetyl)-piperidin-4-yl)-5-fluoro-4H-3,1-benzoxazin-2(1H)-one as an amorphous white powder (HPLC retention time=7.4 min (method A); TLC Rf =0.15 (95:5:0.5 CH2Cl2 : MeOH:NH4OH)).

Workup

  1. customExcess HCl was removed
  2. customby bubbling argon though the mixture for 15 min
  3. additionEther (125 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-afb397eaa062464ab618e778898fe313
Source dataset
uspto-grants-2000_07
Patent number
US06090805

Reaction notes

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