HCID 70620535, compound → HCID 86735071, compound
Reaction equation
Cl.CN(C)[C@H]1[C@H](O)C(C)(C)OC2C=CC=CC1=2.Cl.[C:19]([NH:23][C@H:24]1[C@H:29]([OH:30])[C:28]([CH3:32])([CH3:31])[O:27][C:26]2[CH:33]=[CH:34][CH:35]=[CH:36][C:25]1=2)(C)([CH3:21])[CH3:20].Cl.O1CCN([C@H]2[C@H](O)C(C)(C)OC3C=CC=CC2=3)CC1>>[CH:19]([NH:23][C@H:24]1[C@H:29]([OH:30])[C:28]([CH3:32])([CH3:31])[O:27][C:26]2[CH:33]=[CH:34][CH:35]=[CH:36][C:25]1=2)([CH3:21])[CH3:20]Participants
Procedure
3,4-Epoxy-3,4-dihydro-2,2-dimethyl-2H-benzo[b]pyran (10.00g.) prepared as described by R. Livingstone, J. Chem Soc., 76, (1962), was treated with isopropylamine (12 ml: an excess) in refluxing ethanol (50 ml.) for 16 hours. Th solution was then evaporated to dryness in vacuo to give an off-white solid (13.00g.). This residue was dissolved in diethyl ether and treated with ethereal hydrogen chloride to give a crystalline hydrochloride (12.06g). Re-crystallisation from ethanol/diethyl ether yielded trans-4-isopropyl-anino-3, 4-dihydro-2,2-dimethyl-2H -benzo[b]pyran-3-olhydrochloride as colourless crystals, m.p. 172°-174°. Similarly prepared were trans-4-dimethylamino-3,4-dihydro-2,2-dimethyl-2H-benzo[b]pyran-3-ol hydrochloride as colourless crystals m.p. 175°-176°, trans-4-t-butylamino-3,4-dihydro-2,2-dimethyl-2H-benzo[b]pyran-3-ol hydrochloride as colourless cyrstals m.p. 239°-241°, trans-4-morpholino-3,4-dihydro-2,2-dimethyl-2H-benzo[b]pyran-3-ol hydrochloride m.p. 181°-187°.
Workup
- customSimilarly prepared
Sources & evidence
- ORD record
- ord-7daa3b6dc12b449eb614f3728dea991f
- Source dataset
- uspto-grants-1977_09
- Patent number
- US04048317
Reaction notes
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