Sodium Hydroxide → Ammonia

HRID 2110805Notes

Reaction equation

HRID 2110805 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[Cl:15])[O:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.[CH:16]([CH:18]1[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>O1CCCC1.C(O)(=O)C>[NH3:9].[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[Cl:15])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:16][CH:18]2[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[CH2:19]2)[CH2:8][CH2:7]1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 37320424-(3,4-Dichlorophenoxy)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 99644481-Boc-piperidine-3-carboxaldehyde

Product 2

HCID 222AmmoniaHCID 68850398HCID 68850398, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(3,4-Dichlorophenoxy)piperidine (1 g) and 1,1-dimethylethyl 3-formyl-1-piperidinecarboxylate (Bioorg. Med. Chem. Lett., 1998, 8, 1595) were combined in tetrahydrofuran (4 ml) at 0° C., acetic acid (0.25 ml) was added and the mixture was stirred for 10 min, then at RT for 5 min. Sodium triacetoxyborohydride (1.25 g) was added in two portions and the resulting mixture was stirred for 16 h. Sodium hydroxide solution (2M) was added to neutralize the acid. The mixture was extracted with diethyl ether, the extracts were dried, filtered and evaporated to give an oil which was chromatographed eluting with dichloromethane:methanol:aqueous ammonia (97:2:1) to give the subtitle compound (1.63 g).

Workup

  1. waitat RT for 5 min
  2. stirringthe resulting mixture was stirred for 16 h
  3. extractionThe mixture was extracted with diethyl ether
  4. customthe extracts were dried
  5. filtrationfiltered
  6. customevaporated
  7. customto give an oil which
  8. customwas chromatographed
  9. washeluting with dichloromethane

Sources & evidence

ORD record
ord-6cbafeb81ca940fb96f8ae5585dd54cf
Source dataset
uspto-grants-2009_04
Patent number
US07517989B2

Reaction notes

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