Sodium Carbonate → (+/-)-N-[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl]-N'-(2-pyrimidinyl)-1,2-ethanediamine dihydrochloride hemihydrate

HRID 974955Notes

Reaction equation

HRID 974955 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][NH2:15].[Cl:16][C:17]1[N:22]=[CH:21][CH:20]=[CH:19][N:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[OH2:1].[ClH:16].[ClH:16].[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][NH:15][C:17]1[N:22]=[CH:21][CH:20]=[CH:19][N:18]=1.[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][NH:15][C:17]1[N:22]=[CH:21][CH:20]=[CH:19][N:18]=1.[ClH:16].[ClH:16]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 744042-ChloropyrimidineHCID 131719474HCID 131719474, compound

Product 1

HCID 67873486(+/-)-N-[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl]-N'-(2-pyrimidinyl)-1,2-ethanediamine dihydrochloride hemihydrateYield 67.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7.4 g of N1 -[(3,4-dihydro-2H-1-benzopyran-2-yl) methyl]-1,2-ethanediamine, 4.1 g 2-chloropyrimidine, 4.2 g of sodium carbonate and 50.6 ml of ethanol was stirred for 4 hours at reflux temperature. The reaction mixture was evaporated. The residue was purified by column chromatography (silica gel; CHCl3 /CH3OH 90:10). The eluent of the desired fraction was evaporated and the residue was converted into the hydrochloride salt in 2-propanol. The salt was filtered off and dried in vacuo, yielding 4.4 g (33.3 %) of (±)-N-[(3,4-dihydro-2H-1-benzopyran-2-yl) methyl]-N'-(2-pyrimidinyl)-1,2-ethanediamine dihydrochloride hemihydrate; mp. 192.7° C. (comp. 1).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. customThe residue was purified by column chromatography (silica gel; CHCl3 /CH3OH 90:10)
  4. customThe eluent of the desired fraction was evaporated
  5. filtrationThe salt was filtered off
  6. customdried in vacuo

Sources & evidence

ORD record
ord-570d700232b5450fad641d28c13d309f
Source dataset
uspto-grants-1997_03
Patent number
US05607949

Reaction notes

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