Water → HCID 19360594, compound

HRID 376976Notes

Reaction equation

[H-].[Na+].[CH2:3]([OH:7])[CH2:4][CH2:5][OH:6].[CH2:8]([C:15]([N:30]([CH3:32])[CH3:31])([CH2:28][CH3:29])[C:16]([C:18]1[CH:23]=[CH:22][C:21](OC)=[C:20]([O:26][CH3:27])[CH:19]=1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O>CC(N(C)C)=O>[CH2:8]([C:15]([N:30]([CH3:31])[CH3:32])([CH2:28][CH3:29])[C:16]([C:18]1[CH:23]=[CH:22][C:21]([O:6][CH2:5][CH2:4][CH2:3][OH:7])=[C:20]([O:26][CH3:27])[CH:19]=1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 120 °C

Procedure

0.40 mol of sodium hydride are suspended in 500 ml of dry dimethylacetamide and 72.3 ml (1.0 mol) of 1,3-propanediol are added dropwise at 0° C. Then 68.3 g (0.20 mol) of 2-benzyl-1-(3,4-dimethoxy-phenyl)-2-dimethylamino-butan-1-one in dimethylacetamide are added dropwise at 0° C. After the solution is stirred at 120° C. for 18 h, the solution is poured into water. The crude product is extracted with ethyl acetate, washed with water, dried over MgSO4, and concentrated. The residue is purified by column chromatography on silica gel with ethyl acetate-hexane (40:60) as an eluent. The structure is confirmed by the 1H-NMR spectrum (CDCl3): δ [ppm] 0.69 (t, 3H), 1.83-1.92 (m, 1H), 2.04-2.16 (m, 3H), 2.38 (s, 6H), 2.40-2.55 (bs, 1H), 3.18-3.23 (m, 2H), 3.88 (s, 3H), 3.89 (t, 2H), 4.27 (t, 2H), 6.84 (d, 1H), 7.15-7.28 (m, 5H), 7.93 (d, 1H), 8.20 (dd, 1H).

Workup

extractionThe crude product is extracted with ethyl acetate
washwashed with water
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue is purified by column chromatography on silica gel with ethyl acetate-hexane (40:60) as an eluent

Sources & evidence

ORD record: ord-4943d5f18cd84f95b4a9c9945a715b9a
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06022906

Reaction notes

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