Thiophene → HCID 57983265, compound

HRID 1869242Notes

Reaction equation

HRID 1869242 reaction equation
[C:1]1([CH2:7][N:8]([CH2:16][C@@H:17]2[CH2:22][CH2:21][NH:20][CH2:19][C@H:18]2[OH:23])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S1[CH:28]=[CH:27][CH:26]=[CH:25]1.[H][H]>CO.[Pd]>[C:1]1([CH2:7][N:8]([CH2:16][C@@H:17]2[CH2:22][CH2:21][N:20]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:19][C@H:18]2[OH:23])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 8030ThiopheneHCID 57983142HCID 57983142, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57983265HCID 57983265, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of intermediate (71) (0.083 mol) and butylaldehyde (7 g) in methanol (300 ml) was hydrogenated with palladium-on-carbon (10%) (2 g) as a catalyst in the presence of a thiophene solution (3 ml). After uptake of hydrogen (1 equivalent), the catalyst was filtered over celite and the filtrate was evaporated. The residue was dissolved in aqueous HCl 2N (500 ml). The mixture was washed with toluene and then separated into its layers. The aqueous layer was basified with 50% aqueous NaOH and then extracted three times with toluene. The combined organic layer was dried, filtered and the solvent was evaporated, yielding 29 g of (trans)-4-[[bis(phenylmethyl)amino]-methyl]-1-butyl-3-piperidinol (intermediate 72).

Workup

  1. customthe filtrate was evaporated
  2. dissolutionThe residue was dissolved in aqueous HCl 2N (500 ml)
  3. washThe mixture was washed with toluene
  4. customseparated into its layers
  5. extractionextracted three times with toluene
  6. customThe combined organic layer was dried
  7. filtrationfiltered
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-dadd9bae7a0548678cddb2f7e8fa0574
Source dataset
uspto-grants-2009_12
Patent number
US07638535B2

Reaction notes

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