Dimethylformamide → (+)-3-[4-[N-n-Propyl-N-(5-Methoxychroman-3-Yl)Amino]Butyl]-2,4-Dioxo-3-Azaspiro[4.5]Decane (Oxalate)

HRID 1109795Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH:6]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[C:22](=[O:23])[C:21]3([CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH2:20][C:19]1=[O:29])[CH2:7][O:8]2.I[CH2:31][CH2:32][CH3:33].[C:34](=[O:37])([O-:36])[O-].[K+].[K+].CN(C)C=[O:43]>O>[C:19]([OH:29])(=[O:43])[C:34]([OH:36])=[O:37].[CH2:31]([N:13]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[C:22](=[O:23])[C:21]2([CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[CH2:20][C:19]1=[O:29])[CH:6]1[CH2:5][C:4]2[C:9](=[CH:10][CH:11]=[CH:12][C:3]=2[O:2][CH3:1])[O:8][CH2:7]1)[CH2:32][CH3:33]

Participants

Conditions

Temperature: 60 °C

Procedure

1.5 mmol of the compound prepared in Example 1 are dissolved in 10 ml of dimethylformamide in the presence of 4.4 mmol of 1-iodopropane and 4.4 moles of potassium carbonate. After stirring for 24 hours at 60° C., the solvent is evaporated and the crude reaction mixture is taken up in 10 ml of water and extracted with dichloro-methane. The organic phase is dried and evaporated and the expected product is obtained after purification by chromatography on a silica column. It is salified with oxalic acid.

Workup

customthe solvent is evaporated
customthe crude reaction mixture
extractionextracted with dichloro-methane
customThe organic phase is dried
customevaporated

Sources & evidence

ORD record: ord-6365452dd5324e1d97766f2665960ab2
Source dataset: uspto-grants-1994_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05322944

Reaction notes

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