Hydrochloric Acid → HCID 66781969, compound

HRID 1468537Notes

Reaction equation

HRID 1468537 reaction equation
Cl.[C:2]1([C@H:8]([NH:10][C@H:11]([CH3:22])[CH2:12][C:13]2[CH:14]=[C:15]([CH2:19][C:20]#[N:21])[CH:16]=[CH:17][CH:18]=2)[CH3:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].Cl.[OH-].[Na+]>CO.O.O.O.O.O.O.[Co](Cl)Cl>[NH2:21][CH2:20][CH2:19][C:15]1[CH:14]=[C:13]([CH2:12][C@H:11]([NH:10][C@@H:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH3:9])[CH3:22])[CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 66781684HCID 66781684, compound

Product 1

HCID 66781969HCID 66781969, compound

Reagents, catalysts & solvents 2

HCID 517166Dichlorocobalt hexahydrateCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of {3-[(R)-2-((R)-1-phenylethylamino)propyl]phenyl}-acetonitrile hydrochloride salt (2.00 g, 6.35 mmol) and cobalt(II) chloride hexahydrate (4.27 g, 18.0 mmol) in MeOH (40.0 mL) at 0° C. was added sodium tetrahydroborate (2.72 g, 71.8 mmol) portion-wise (reaction was exothermic). The reaction mixture was stirred for 1 h at room temperature and then concentrated aqueous hydrochloric acid was added and stirring was continued until the solid that had formed was broken-up. The mixture was then made basic by addition of aqueous sodium hydroxide (1 M). This mixture was filtered and the filtrate was extracted with DCM (50 mL). The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound, which as used in the next reaction without further purification.

Workup

  1. stirringstirring
  2. customthat had formed
  3. filtrationThis mixture was filtered
  4. extractionthe filtrate was extracted with DCM (50 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-be911de9bcd64d2487242afcea455c96
Source dataset
uspto-grants-2015_04
Patent number
US09000173B2

Reaction notes

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