Ammonia → HCID 18694134, compound

HRID 1871000Notes

Reaction equation

HRID 1871000 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][CH2:3][CH:2]1[CH2:11][NH:12][CH2:13][CH2:14][C:15]#[N:16].N.[H][H]>CO.[Ni]>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][CH2:3][CH:2]1[CH2:11][NH:12][CH2:13][CH2:14][CH2:15][NH2:16]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 18694193HCID 18694193, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18694134HCID 18694134, compoundYield 90.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of intermediate (16-c) (0.12 mol) in methanol saturated with ammonia (500 ml) was hydrogenated with Raney nickel (6 g) as a catalyst After uptake of hydrogen (2 eq.), the catalyst was filtered off and the filtrate was evaporated. The residue was purified by distillation, yielding 24 g (90.8%) of (±)-N-[(3,4-dihydro-2H-benzopyran-2-yl)methyl]-1,3-propanediamine (interm. 17-c).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. distillationThe residue was purified by distillation

Sources & evidence

ORD record
ord-b27ff2e49d44450aa6ba17ca258c3bc7
Source dataset
uspto-grants-2000_08
Patent number
US06100268

Reaction notes

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