Butanal → HCID 15482224, compound

HRID 528907Notes

Reaction equation

[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([NH2:11])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[CH:12](=O)[CH2:13][CH2:14][CH3:15]>>[CH2:12]([NH:11][C:9]1[CH:8]=[CH:7][C:6]2[O:1][CH2:2][CH2:3][O:4][C:5]=2[CH:10]=1)[CH2:13][CH2:14][CH3:15]

Participants

Reactant 2

HCID 261Butanal

HCID 891481,4-Benzodioxan-6-ylamine

Product 1

HCID 15482224HCID 15482224, compoundYield 90.4%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 137, 1,4-benzodioxan-6-amine (410 μL, 3.31 mmol) and butyraldehyde (300 μL, 3.31 mmol) were converted to the title compound (620 mg, 83%). 1H NMR (CDCl3) δ 6.77-6.58 (m, 1H), 6.28-5.96 (m, 2H), 4.30-4.12 (m, 4H), 3.04 (t, J=7.2 Hz, 2H), 1.65-1.49 (m, 2H), 1.49-1.37 (m, 2H), 0.95 (t, J=7.4 Hz, 3H); MS(ESI+) m/z 208.3 (M+H)+.

Sources & evidence

ORD record: ord-87d7df05366f4526a83ff8dd3212cc9d
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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