Piperonal → HCID 20817771, compound

HRID 897237Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([F:21])([F:20])[F:19])[CH:16]=3)[O:11][C:10](=[O:22])[CH:9]=2)[CH2:3][CH2:2]1.[CH:23]1[C:28]([CH:29]=O)=[CH:27][C:26]2[O:31][CH2:32][O:33][C:25]=2[CH:24]=1>>[O:33]1[C:25]2[CH:24]=[CH:23][C:28]([CH2:29][N:1]3[CH2:2][CH2:3][CH:4]([NH:7][C:8]4[C:17]5[C:12](=[CH:13][CH:14]=[C:15]([C:18]([F:20])([F:19])[F:21])[CH:16]=5)[O:11][C:10](=[O:22])[CH:9]=4)[CH2:5][CH2:6]3)=[CH:27][C:26]=2[O:31][CH2:32]1

Participants

Reactant 2

HCID 8438Piperonal

HCID 85904484HCID 85904484, compound

Product 1

HCID 20817771HCID 20817771, compoundYield 44%

Procedure

4-(1-Benzo[1,3]dioxol-5-ylmethyl-piperidin-4-ylamino)-6-trifluoromethyl-chromen-2-one was prepared according to a reductive amination procedure using 4-(piperdin-4-ylamino)-6-trifluoromethyl-chromen-2-one (116 mg, 0.373 mmol) and piperonal (62 mg, 0.411 mmol) to provide the title product as a white solid (73 mg, 44%). MS (APCI) m/z 447 [M+H]+, 445 [M−H]+, 481 [M+Cl]+; 1H NMR (300 MHz, DMSO-D6) δ ppm 1.64 (m, 2H) 1.92 (m, J=9.83 Hz, 2H) 2.09 (m, 2H) 2.84 (m, J=11.53 Hz, 2H) 3.51 (m, 1H) 5.34 (s, 1H) 5.99 (s, 2H) 6.76 (d, J=6.44 Hz, 1H) 6.85 (d, J=8.82 Hz, 2H) 7.51 (t, J=9.32 Hz, 2H) 7.92 (dd, J=8.82, 1.70 Hz, 1H) 8.63 (s, 1H).

Workup

custom4-(1-Benzo[1,3]dioxol-5-ylmethyl-piperidin-4-ylamino)-6-trifluoromethyl-chromen-2-one was prepared

Sources & evidence

ORD record: ord-5c3fa4562e584c7786104fe3b334a1ef
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06921821B2

Reaction notes

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