Ammonium Chloride → HCID 58864516, compound

HRID 2355938Notes

Reaction equation

HRID 2355938 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=O.[NH2:13][CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][CH2:15]1.[BH4-].[Na+].[Cl-].[NH4+]>C(O)C>[CH2:20]([N:17]1[CH2:18][CH2:19][CH:14]([NH:13][CH2:7][C:6]2[CH:9]=[C:2]([OH:1])[CH:3]=[CH:4][C:5]=2[N+:10]([O-:12])=[O:11])[CH2:15][CH2:16]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 392115-Hydroxy-2-nitrobenzaldehydeHCID 4158521-Benzyl-4-piperidylamineHCID 4311764Sodium borohydride

Product 1

HCID 58864516HCID 58864516, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

5-Hydroxy-2-nitro-benzaldehyde (5 g, 29.9 mmol) and 4-amino-1-benzylpiperidine (5.6 mL, 29.9 mmol) were combined in ethanol (30 mL). The resulting suspension was stirred at room temperature for 20 min before a solution of sodium borohydride (1.13 g, 29.9 mmol) in ethanol (10 mL) was added dropwise over 10 min. After the addition was complete, the reaction was stirred at room temperature for 1 h, cooled to 0° C. and concentrated ammonium chloride added to the reaction mixture until no bubbling was observed. The solvents were evaporated in vacuo and the resultant crude mixture was dissolved in water (30 mL) and methylene chloride (40 mL). The layers were separated and the organic layer washed with water (2×), brine (2×), dried over sodium sulfate, filtered, and concentrated to afford 5.8 g (57%) of the desired product. LC/MS: tR=0.95 min, 342.27 (MH)+.

Workup

  1. additionwas added dropwise over 10 min
  2. additionAfter the addition
  3. temperaturecooled to 0° C.
  4. customThe solvents were evaporated in vacuo
  5. dissolutionthe resultant crude mixture was dissolved in water (30 mL)
  6. customThe layers were separated
  7. washthe organic layer washed with water (2×), brine (2×)
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-685314c88ed94acaaedb612db194ccf0
Source dataset
uspto-grants-2010_07
Patent number
US07754732B2

Reaction notes

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