Hydrochloric Acid → HCID 59923424, compound

HRID 2298115Notes

Reaction equation

HRID 2298115 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:23]=[CH:22][C:21](/[CH:24]=[C:25]2/[CH:26]=[N:27][CH2:28][CH2:29][CH2:30]/2)=[CH:20][C:5]=1[C:6]([NH:8][CH2:9][C:10]12[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]3)[CH2:11]1)[CH2:17]2)=[O:7].Cl>CO>[Cl:3][C:4]1[CH:23]=[CH:22][C:21](/[CH:24]=[C:25]2/[CH2:26][NH:27][CH2:28][CH2:29][CH2:30]/2)=[CH:20][C:5]=1[C:6]([NH:8][CH2:9][C:10]12[CH2:11][CH:12]3[CH2:13][CH:14]([CH2:15][CH:16]([CH2:18]3)[CH2:17]1)[CH2:19]2)=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 70155592HCID 70155592, compound

Product 1

HCID 59923424HCID 59923424, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Sodium borohydride (0.009 g) in methanol (0.5 ml) was added to a solution of 2-chloro-5-[(E)-(5,6-dihydro-3(4H)-pyridinylidene)methyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.046 g, Example 88a,) in methanol (1.5 ml). The reaction mixture was stirred for 4 h under an atmosphere of nitrogen at room temperature. Concentrated hydrochloric acid (0.01 ml) was added and the mixture was evaporated under reduced pressure. An aqueous solution of sodium hydroxide (2M, 2 ml) was added to rebasify the residue followed by water (10 ml) and dichloromethane (10 ml). The layers were partitioned and the aqueous layer was extracted further with dichloromethane (2×10 ml). The organic extracts were combined, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound as a white powder (0.024 g).

Workup

  1. customthe mixture was evaporated under reduced pressure
  2. additionAn aqueous solution of sodium hydroxide (2M, 2 ml) was added
  3. customThe layers were partitioned
  4. extractionthe aqueous layer was extracted further with dichloromethane (2×10 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4e1011869ac4496da8de2ed20889c293
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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