HCID 70620535, compound → HCID 86735071, compound

HRID 2420280Notes

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]([CH:41]2C(C(C)C)CCC(C)C2)([CH:31]2C(C(C)C)CCC(C)C2)[O:27][C:26]2[CH:51]=[CH:52][CH:53]=[CH:54][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]([CH3:41])([CH3:31])[O:27][C:26]2[CH:51]=[CH:52][CH:53]=[CH:54][C:25]1=2)([CH3:21])[CH3:20]

Participants

Reactant 3

HCID 70620535HCID 70620535, compound

HCID 70620584HCID 70620584, compound

HCID 70620944HCID 70620944, compound

Product 1

HCID 86735071HCID 86735071, compound

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. The 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-amino-3, 4-dihydro-2,2-dimethyl-2H-benzo[b]pyran-3-ol hydrochloride 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-dimenthyl-2H-benzo[b] pyran-3-ol hydrochloride as colourless crystals 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-b571fc3d875e40a6b84162acb04b4a08
Source dataset: uspto-grants-1978_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04110347

Reaction notes

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