Hydrochloric Acid → HCID 15027725, compound

HRID 373153Notes

Reaction equation

HRID 373153 reaction equation
C=O.[OH:3][CH:4]([C:18]1[CH:23]=[CH:22][C:21]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:20][CH:19]=1)[CH2:5][CH2:6][CH2:7][NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[N:12]=1.[BH4-].[Na+].Cl.[C:32](=O)([O-])O.[Na+]>CO>[OH:3][CH:4]([C:18]1[CH:19]=[CH:20][C:21]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:22][CH:23]=1)[CH2:5][CH2:6][CH2:7][N:8]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[N:12]=1)[CH3:32]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 15027724HCID 15027724, compound

Product 1

HCID 15027725HCID 15027725, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

5.19 ml of formalin was added to a solution of 2.12 g (free compound: 6.12 mmol) of N-[4-[1-hydroxy-4-[2-(6-methyl-2-pyridyl)ethylamino]butyl]phenyl]methanesulfonamide obtained in Example 3-(4) in 20 ml of methanol. The mixture was refluxed for 30 min. The mixture was cooled at 0° C. and 0.81 g of sodium borohydride was added in small portions thereto. The mixture was stirred at 0° C. for 20 min. 36 ml of 1N hydrochloric acid was added thereto to acidify it. The solution thus obtained was poured into 100 ml of a saturated sodium hydrogencarbonate solution. After extraction with dichloromethane, the organic layer was concentrated to give 2.16 g (yield: 94%) of the intended compound.

Workup

  1. temperatureThe mixture was refluxed for 30 min
  2. customThe solution thus obtained
  3. extractionAfter extraction with dichloromethane
  4. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-76416c04c93c460d8edf06ba287890a1
Source dataset
uspto-grants-1992_11
Patent number
US05162347

Reaction notes

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