Dimethylformamide dimethyl acetal → HCID 68578480, compound

HRID 273064Notes

Reaction equation

HRID 273064 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([C:22]([NH2:24])=[O:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.CO[CH:27](OC)[N:28]([CH3:30])[CH3:29]>>[CH3:27][N:28]([CH:30]=[N:24][C:22]([C:16]1([C:13]2[CH:14]=[CH:15][C:10]([O:9][CH2:8][CH2:7][CH2:6][N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:11][CH:12]=2)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)=[O:23])[CH3:29]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 11493681HCID 11493681, compound

Product 1

HCID 68578480HCID 68578480, compoundYield 100%

Procedure

4-[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carboxylic acid amide (0.561 g, 1.69 mmol) and N,N-dimethylformamide dimethyl acetal (5 mL) were combined and heated at reflux for 4 hours. The reaction mixture was concentrated in vacuo and azeotroped with toluene (2×10 mL) to provide the title compound (0.655 g, 100%) as a brown solid. 1H NMR (400 MHz, CDCl3) δ 1.80-1.85 (m, 4H), 1.85-1.95 (m, 2H), 2.0-2.10 (m, 2H), 2.6-2.78 (m, 8H), 3.0 (s, 3H), 3.05 (s, 3H), 3.60 (m, 2H), 3.90 (m, 2H), 4.0 (t, 2H), 6.80 (d, 2H), 7.35 (d, 2H), 8.30 (s, 1H). LRMS APCI+ m/z 388 [MH]+.

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customazeotroped with toluene (2×10 mL)

Sources & evidence

ORD record
ord-5206c6b448bb44eab1a847a647a43456
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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