Ethylenediamine → trans-4-(2-Aminoethylamino)-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-ol

HRID 847167Notes

Reaction equation

HRID 847167 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[CH:9]3[O:14][CH:8]3[C:7]=2[CH:15]=1)#[N:2].[CH2:16]([NH2:19])[CH2:17][NH2:18]>C(O)C>[NH2:18][CH2:17][CH2:16][NH:19][C@@H:8]1[C:7]2[CH:15]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=2[O:11][C:10]([CH3:13])([CH3:12])[C@H:9]1[OH:14]

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 108673602,2-Dimethyl-3,4-epoxy-6-cyanochroman

Product 1

HCID 15680853trans-4-(2-Aminoethylamino)-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-olYield 111.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 6-cyano-3,4-epoxy-3,4-dihydro-2,2-dimethyl-2H-benzopyran (1.2 g, 5.97 mmol) (prepared according to Evans et al., J. Med. Chem., 1983, 26, 1582 and J. Med. Chem., 1986, 29, 2194) in ethanol (7.0 mL), ethylenediamine (2.4 mL, 35.8 mmol) was added at room temperature and the reaction mixture was stirred at room temperature for 36 hours. The solvent was removed under reduced pressure and the residue was further dried by use of vacuum pump to yield the title A compound (1.74 g, >100%) as a colorless foam. This material was used for the next reaction without any purification.

Workup

  1. additionwas added at room temperature
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was further dried by use of vacuum pump

Sources & evidence

ORD record
ord-b5458a96f21d44c1ba60847dd71cb7fa
Source dataset
uspto-grants-1992_08
Patent number
US05140031

Reaction notes

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