Benzylamine → HCID 18694202, compound

HRID 1870987Notes

Reaction equation

HRID 1870987 reaction equation
[O:1]1[C:6]2[C:7]3[CH2:13][CH2:12][CH2:11][C:8]=3[CH:9]=[CH:10][C:5]=2[CH2:4][CH2:3][CH:2]1[CH:14]=O.[C:16]1([CH2:22][NH2:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[H][H]>O(C(C)C)C(C)C.CN(C)C(=O)C.[Pd]>[C:16]1([CH2:22][NH:23][CH2:14][CH:2]2[CH2:3][CH2:4][C:5]3[CH:10]=[CH:9][C:8]4[CH2:11][CH2:12][CH2:13][C:7]=4[C:6]=3[O:1]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 3

HCID 7504BenzylamineHCID 18694138HCID 18694138, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18694202HCID 18694202, compoundYield 73.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 7914Diisopropyl EtherSolventHCID 31374DimethylacetamideSolvent

Procedure

A mixture of intermediate (5-a) (0.03 mol) and benzenemethanamine (0.073 mol) in 2,2'-oxybispropane (250 ml) and N,N-dimethylacetamide (10 ml) was hydrogenated with palladium on activated carbon (10%) (1 g) as a catalyst. After uptake of hydrogen (1 eq.), the catalyst was filtered off. The filtrate was evaporated. The residue was stirred in a mixture of water and 1,1'-oxybisethane. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated, yielding 6.5 g of (±)-2,3,4,7,8,9-hexahydro-N-(phenylmethyl)cyclopenta[h]-1-benzopyran-2-methanamine (interm. 14-a).

Workup

  1. customThe filtrate was evaporated
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-9cc9eb9c65df48a98d6e82bac0fff82f
Source dataset
uspto-grants-2000_08
Patent number
US06100268

Reaction notes

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