HCID 12050656, compound → HCID 9882403, compound

HRID 1635626Notes

Reaction equation

HRID 1635626 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[C:16]([NH:18][CH2:19][CH2:20][NH:21]C(=O)OCC1C=CC=CC=1)=[O:17]>CO.[Pd]>[NH2:21][CH2:20][CH2:19][NH:18][C:16]([C@@H:11]1[CH2:12][CH2:13][CH2:14][CH2:15][N:10]1[C:2]1[O:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=1)=[O:17]

Participants

4

Reactant 1

HCID 12050656HCID 12050656, compound

Product 1

HCID 9882403HCID 9882403, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Benzyl N-[2-([(2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinyl]carbonylamino)ethyl]carbamate (480.6 mg) [see Preparation 4] was dissolved in methanol (20 ml) and 10% palladium on charcoal (48 mg) was added. The reaction mixture was then hydrogenated at 4 atmospheres (60 p.s.i.) at room temperature for 3 hours, after which time the mixture was filtered and the solvent removed under reduced pressure. The product was then azeotroped with dichloromethane to afford (2S)-N2-(2-aminoethyl)-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxamide (296 mg) as a colourless liquid.

Workup

  1. filtrationafter which time the mixture was filtered
  2. customthe solvent removed under reduced pressure
  3. customThe product was then azeotroped with dichloromethane

Sources & evidence

ORD record
ord-d4bf155ab0a249c68978f2e159b771e5
Source dataset
uspto-grants-2003_01
Patent number
US06509464B1

Reaction notes

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