Dimethylformamide → 5,6-Dihydro-6-hydroxy-5,5-dimethyl-7-piperidin-1-yl-7H-thieno[3,2-b]pyran

HRID 257220Notes

Reaction equation

HRID 257220 reaction equation
Br[CH:2]1[C:7]([CH3:9])([CH3:8])[O:6][C:5]2[CH:10]=[CH:11][S:12][C:4]=2[CH:3]1O.[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.CN(C)C=[O:23]>>[OH:23][CH:2]1[C:7]([CH3:9])([CH3:8])[O:6][C:5]2[CH:10]=[CH:11][S:12][C:4]=2[CH:3]1[N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 8082PiperidineHCID 149864866-bromo-5,6-dihydro-7-hydroxy-5,5-dimethyl-7H-thieno[3,2-b]pyran

Product 1

HCID 149865195,6-Dihydro-6-hydroxy-5,5-dimethyl-7-piperidin-1-yl-7H-thieno[3,2-b]pyran

Procedure

The title compound was prepared as described in Example 18 starting with 6-bromo-5,6-dihydro-7-hydroxy-5,5-dimethyl-7H-thieno[3,2-b]pyran (1.5 g, 5.7 mmol) and piperidine (1.7 mL, 17.1 mmol) in N,N-dimethylformamide (25 mL) to give an off white solid, 0.977 (64%): mp 68°-70°C.; IR (KBr): 2937, 1549 and 1396 cm-1 ; MS: m/z 162 (MH+); 1H NMR (CDCl3): δ 1.20 (s, 3H), 1.50 (s, 3H), 1.52 (m, 2H), 1.61 (m, 4H), 2.65 (m, 2H), 2.78 (m, 2H), 3.20 (bs, 1H, exchanges with D2O), 3.55 (d, J=9.3 Hz, 1H), 3.68 (d, J=9.3 Hz, 1H), 6.58 (d, J=5.4 Hz, 1H) and 7.04 (d, J=5.4 Hz, 1H).

Sources & evidence

ORD record
ord-bf65aee9980f4e37b389a082a55ff0d0
Source dataset
uspto-grants-1993_11
Patent number
US05260453

Reaction notes

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