Hydrochloric Acid → HCID 131719475, compound

HRID 1736353Notes

Reaction equation

HRID 1736353 reaction equation
O.[ClH:2].Cl.[O:4]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][C@@H:5]1[CH2:14][NH:15][CH2:16][CH2:17][CH2:18][NH:19][C:20]1[N:25]=[CH:24][CH:23]=[CH:22][N:21]=1.[O:26]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[CH2:29][CH2:28][C@@H:27]1[CH2:36][NH:37][CH2:38][CH2:39][CH2:40][NH:41][C:42]1[N:47]=[CH:46][CH:45]=[CH:44][N:43]=1.Cl.Cl.Cl.[H][H]>CO.CC(O)C.[Pd]>[OH2:4].[ClH:2].[ClH:2].[O:26]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[CH2:29][CH2:28][C@@H:27]1[CH2:36][NH:37][CH2:38][CH2:39][CH2:40][NH:41][C:42]1[NH:47][CH2:46][CH2:45][CH2:44][N:43]=1.[O:4]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][C@@H:5]1[CH2:14][NH:15][CH2:16][CH2:17][CH2:18][NH:19][C:20]1[NH:25][CH2:24][CH2:23][CH2:22][N:21]=1.[ClH:2].[ClH:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 131719476HCID 131719476, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131719475HCID 131719475, compoundYield 296.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of 3.6 g of (-)-(R)-N-[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl]-N'-(2-pyrimidinyl)-1,3-propanediamine dihydrochloride hemihydrate in 150 ml of methanol and 20 ml of 2-propanol saturated with HCl was hydrogenated in the presence of 1.5 g of palladium-on-charcoal catalyst (2%). After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The product was crystallized from acetonitrile, filtered off and dried, yielding 2.7 g (74.0%) of (-)-(R)-N-[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl]-N'-(1,4,5,6-tetrahydro-2-pyrimidinyl)-1,3-propanediamine dihydrochloride hemihydrate; mp. 200.2° C. [α]D20 =-60.97° (conc.=1% in CH3OH) (comp. 62).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe product was crystallized from acetonitrile
  4. filtrationfiltered off
  5. customdried

Sources & evidence

ORD record
ord-eb17b2ca21a248f7ba70060fd7d91b74
Source dataset
uspto-grants-1996_07
Patent number
US05541180

Reaction notes

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