Ammonium formate → 5-Amino-1-tetrahydropyran-2-ylindole

HRID 1418032Notes

Reaction equation

HRID 1418032 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][O:14]1)[CH:8]=[CH:7]2)([O-])=O.C([O-])=O.[NH4+]>CO>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][O:14]1)[CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 545254335-Nitro-1-tetrahydropyran-2-ylindole

Product 1

HCID 543799705-Amino-1-tetrahydropyran-2-ylindoleYield 95.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

17 g of 5-nitro-1-tetrahydropyran-2-ylindole are dissolved in 170 ml of methanol and then 3 g of 10% Pd-on-charcoal and then, portionwise at 0° C., 20.6 g of ammonium formate are added. After stirring for 1 hour 30 at room temperature, the reaction mixture is filtered and the filtrate is evaporated to dryness. The residue is taken up in 300 ml of ethyl acetate. The solution is washed with 800 ml of water, dried over sodium sulphate and evaporated to dryness. 14.2 g of 5-amino-1-tetrahydropyran-2-ylindole are obtained in the solid form. A sample is purified by chromatography on a column of silica gel eluted with a 3/1 (v/v) cyclohexane/ethyl acetate mixture, to provide (Compound 29). 1H NMR (DMSO): 1.30-2.20 (m, 6H), 3.59-3.93 (m, 2H), 4.72 (m, 2H), 5.41 (dd, J=1.8, 12.0, 1H), 6.16 (d, J=3.2, 1H), 6.52 (dd, J=2.0, 8.6, 1H), 6.66 (d, J=2.0, 1H), 7.20 (d, J=8.6, 1H), 7.27 (d, J=3.2, 1H).

Workup

  1. filtrationthe reaction mixture is filtered
  2. customthe filtrate is evaporated to dryness
  3. washThe solution is washed with 800 ml of water
  4. dry with materialdried over sodium sulphate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-bf6b01a4025e4ce69b9ef398cc521b16
Source dataset
uspto-grants-1999_03
Patent number
US05880135

Reaction notes

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