1,2-Dichloroethane → (4-Hydroxypiperidin-1-yl)(4-styrylphenyl)methanone

HRID 533717Notes

Reaction equation

HRID 533717 reaction equation
C([C:3]1[CH:11]=[C:10](/[CH:12]=[CH:13]/[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O)C.CCN(C(C)C)C(C)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.Cl.[OH:44][CH:45]1[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1>CN(C=O)C.O>[OH:44][CH:45]1[CH2:50][CH2:49][N:48]([C:5]([C:4]2[CH:3]=[CH:11][C:10]([CH:12]=[CH:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:9][CH:8]=2)=[O:7])[CH2:47][CH2:46]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 162124994-Hydroxypiperidinium chlorideHCID 67246536(E)-ethyl 4-styrylbenzoic acid

Product 1

HCID 68723389(4-Hydroxypiperidin-1-yl)(4-styrylphenyl)methanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)-ethyl 4-styrylbenzoic acid (300 mg, 1.3 mmol) and DIPEA (270 uL, 2.1 mmol) in DMF (5 mL) was added EDC (280 mg, 1.5 mmol), HOBt (270 mg, 2.0 mmol) and 4-hydroxypiperidine hydrochloride (258 mg, 1.8 mmol). The reaction was stirred at room temperature for 18 h. The reaction was diluted with water (10 mL) and (4-hydroxypiperidin-1-yl)(4-styrylphenyl)methanone was isolated (390 mg, 98%) as a white solid by vacuum filtration; 1H-nmr (400 MHz, CDCl3) δ 7.58 (d, J=8.0 Hz, 2H), 7.56-7.52 (m, 2H), 7.44-7.34 (m, 5H), 6.95 (d, 1H), 6.89 (d, 1H), 4.21-4.08 (m, 1H), 4.03-3.96 (m, 1H), 3.81-3.48 (m, 1H), 3.47-3.16 (m, 2H), 2.08-1.79 (m, 2H), 1.71-1.42 (m, 2H); LCMS (214 nM) 3.32 min (>98%); MS (ESI) m/z=308.1.

Sources & evidence

ORD record
ord-883d557b2fd64b868c99dfe0003143d9
Source dataset
uspto-grants-2014_10
Patent number
US08853392B2

Reaction notes

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