N,N'-Dimethylethylenediamine → HCID 66579660, compound

HRID 2092670Notes

Reaction equation

[O:1]1[C:5]2([CH2:15][CH2:14][C:8]3([CH2:12][CH2:11][NH:10][C:9]3=[O:13])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.Br[C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][O:26][CH3:27])=[CH:19][CH:18]=1.CNCCNC.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C>[CH3:27][O:26][CH2:25][CH2:24][CH2:23][C:20]1[CH:21]=[CH:22][C:17]([N:10]2[CH2:11][CH2:12][C:8]3([CH2:14][CH2:15][C:5]4([O:4][CH2:3][CH2:2][O:1]4)[CH2:6][CH2:7]3)[C:9]2=[O:13])=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1,4-Dioxa-10-aza-dispiro[4.2.4.2]tetradecan-9-one (276 mg, obtained in example 121, step 3) was dissolved in DMF (18 mL) at r.t. Then, 1-bromo-4-(3-methoxy-propyl)-benzene (599 mg, obtained in example 130, step 2), N,N′-dimethylethylenediamine (sym) (230 mg), Cuprous iodide (373 mg) and K3PO4 (832 mg) were added to the reaction mixture and the mixture was heated to 80° C. for 3 hours. The reaction mixture was cooled, poured into ice/water and was extracted two times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. The title compound was obtained as a yellow liquid (460 mg, 93%) and was used without further purification. MS (m/e): 360.2. [MH+].

Workup

temperatureThe reaction mixture was cooled
extractionwas extracted two times with ethyl acetate
washThe combined organic layers were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
customthe solvent was evaporated

Sources & evidence

ORD record: ord-d3203ce06d50432494f5ff56d36e8294
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440710B2

Reaction notes

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