Hydrochloric Acid → HCID 53728481, compound

HRID 273870Notes

Reaction equation

HRID 273870 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:21]2[C:16](=[CH:17][C:18]([CH2:25][C@H:26]([NH:28][CH2:29][CH2:30][O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[O:38][CH2:39][C:40]([F:43])([F:42])[F:41])[CH3:27])=[CH:19][C:20]=2[C:22]([NH2:24])=[O:23])[CH2:15][CH2:14]1)C1C=CC=CC=1.Cl>C(O)C.[Pd]>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:21]2[C:16](=[CH:17][C:18]([CH2:25][C@H:26]([NH:28][CH2:29][CH2:30][O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[O:38][CH2:39][C:40]([F:43])([F:41])[F:42])[CH3:27])=[CH:19][C:20]=2[C:22]([NH2:24])=[O:23])[CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 53713896HCID 53713896, compound

Product 1

HCID 53728481HCID 53728481, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (R)-(-)-1-(4-benzyloxybutyl)-5-[2-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethylamino]propyl]indoline-7-carboxamide (200 mg) in ethanol (3.3 ml) were added a 1N hydrochloric acid (0.8 ml) and 10% palladium on carbon (20 mg), and the mixture was stirred at room temperature for 4 hours under an atmosphere of hydrogen. After the catalyst was filtered off, the filtrate was concentrated under reduced pressure. To the concentrate were added water (12 ml) and sodium carbonate (106 mg), and the mixture was stirred for overnight at room temperature. The precipitated crystals were collected, washed with water, and dried at 50° C. under reduced pressure to give 160 mg of (R)-(-)-1-(4-hydroxybutyl)-5-[2-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethylamino]propyl]indoline-7-carboxamide melting at 116°-118° C.

Workup

  1. filtrationAfter the catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the concentrate were added water (12 ml) and sodium carbonate (106 mg)
  4. stirringthe mixture was stirred for overnight at room temperature
  5. customThe precipitated crystals were collected
  6. washwashed with water
  7. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-ee0e401d09b943509ec5779e212e075b
Source dataset
uspto-grants-1995_02
Patent number
US05387603

Reaction notes

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