Formaldehyde → HCID 24984258, compound

HRID 1724068Notes

Reaction equation

[NH:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:24]=[CH:23][C:10]([CH2:11][N:12]3[CH2:16][C:15]4([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]4)[O:14][C:13]3=[O:22])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[CH2:25]=O>C(O)=O>[CH3:25][N:1]1[CH2:2][CH:3]=[C:4]([C:7]2[CH:8]=[CH:9][C:10]([CH2:11][N:12]3[CH2:16][C:15]4([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]4)[O:14][C:13]3=[O:22])=[CH:23][CH:24]=2)[CH2:5][CH2:6]1

Participants

Conditions

Temperature: 100 °C

Procedure

3-[4-(1,2,3,6-Tetrahydro-pyridin-4-yl)-benzyl]-1-oxa-3-aza-spiro[4.5]decan-2-one (31 mg, 0.095 mmol), formaldehyde (1.5 mL) and formic acid (1.5 mL) were mixed and heated at 100° C. for 2 hours. The reaction mixture was concentrated; the residue was dissolved in DCM (2 mL) and neutralized by adding saturated NaHCO3. The aqueous phase was extracted with DCM (2×3 mL). The combined organic phase was dried over sodium sulfate and concentrated in vacuo. The crude residue was purified on silica gel eluting with 2M NH3 in methanol/DCM (4: 96) to give the product as off-white solid (25 mg, 78%). 1H NMR (300 MHz, CDCl3): δ (ppm) 7.39 (d, 2H), 7.23 (d, 2H), 6.09 (br, 1H), 4.41 (s, 2H), 3.13 (br, 2H), 3.09 (s, 2H), 2.7 (m, 2H), 2.59 (br, 2H), 2.42 (s, 3H), 1.78 (m, 4H), 1.54 (m, 6H).

Workup

concentrationThe reaction mixture was concentrated
dissolutionthe residue was dissolved in DCM (2 mL)
additionby adding saturated NaHCO3
extractionThe aqueous phase was extracted with DCM (2×3 mL)
dry with materialThe combined organic phase was dried over sodium sulfate
concentrationconcentrated in vacuo
customThe crude residue was purified on silica gel eluting with 2M NH3 in methanol/DCM (4: 96)

Sources & evidence

ORD record: ord-bad979ec82cd4c4f9b4ff2eba330798a
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07485722B2

Reaction notes

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