Ethanol → HCID 86739749, compound
Reaction equation
Cl.[Cl:2][CH2:3][CH2:4][CH2:5][NH2:6].[OH-].[Na+].[C:9]([C:11]1[CH:23]=[CH:22][C:14]2[O:15][C:16]([CH3:21])(C)[CH:17]3[O:19][CH:18]3[C:13]=2[CH:12]=1)#[N:10].[CH2:24](O)C>>[ClH:2].[C:9]([C:11]1[CH:23]=[CH:22][C@@H:14]2[O:15][C@H:16]([CH3:21])[C:17]([CH3:24])([OH:19])[C:18]([NH:6][CH2:5][CH2:4][CH2:3][Cl:2])=[C:13]2[CH:12]=1)#[N:10]Participants
Procedure
To a stirred solution of chloropropylamine hydrochloride (2.0 g) and sodium hydroxide pellets (0.5 g) in ethanol (150 ml) was added 6-cyano-3,4-epoxy-3,4-dihydro-2,2-dimethyl-2H-benzo[b]pyran (2.0 g, prepared as described in U.K. patent 1,511,187, Example 7). The reaction mixture was stirred at room temperature for 15 days and monitored by TLC. The solution was filtered and evaporated, and the resulting gum (1.74 g) chromatographed on 200 g silica gel with elution by ethyl acetate. The early, chromatographically homogeneous fractions were combined (1.16 g), and, dissolved in the minimum quantity of ethanol required, were treated with ethereal anhydrous HCl to give the title compound as a white powder (0.54 g) of mp 250°-253° C.; NMR (in DMSOd6) δ1.11 (s), 1.45 (s), 2.25 (distorted t, J=5, 5 Hz), 3.08 (br multiplet), 3.76 (t, J=5, 5 Hz overlapped with m, 3H), 4.03 (d, J=9 Hz), 4.46 (d, J=9 Hz), 7.03 (d, J=8 Hz), 7.74 (g, J=8, 2 Hz), 8.47 (d, J=2 Hz). Anal. Calcd. for C15H20N2O2Cl2 :C, 54.39; H, 6.09; N, 8,46; Cl, 21.41. Found: C, 54.36; H, 6.19; N, 8.33; Cl, 21.50%.
Workup
- filtrationThe solution was filtered
- customevaporated
- customthe resulting gum (1.74 g) chromatographed on 200 g silica gel with elution by ethyl acetate
- dissolutiondissolved in the minimum quantity of ethanol
- additionwere treated with ethereal anhydrous HCl
Sources & evidence
- ORD record
- ord-9bc58b927f034360990d9990eb809124
- Source dataset
- uspto-grants-1984_11
- Patent number
- US04481213
Reaction notes
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