Tripropylamine → HCID 54106116, compound

HRID 2416690Notes

Reaction equation

HRID 2416690 reaction equation
[C:1]([CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=1[CH2:20][NH:21][CH2:22][C:23]([F:26])([F:25])[F:24])[CH2:6][C:7]([O:9][CH3:10])=[O:8])(OC)=[O:2].C(N(CCC)CCC)CC>>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]2[CH2:11][CH:5]([CH2:6][C:7]([O:9][CH3:10])=[O:8])[C:1](=[O:2])[N:21]([CH2:22][C:23]([F:26])([F:25])[F:24])[CH2:20][C:13]=2[CH:14]=1

Participants

3

Reactant 2

HCID 7616TripropylamineHCID 10643299HCID 10643299, compound

Product 1

HCID 54106116HCID 54106116, compoundYield 92.4%

Procedure

A mixture of methyl (±)-3-carbomethoxy-4-[2-(2,2,2-trifluoroethylamino)methyl-4-methoxyphenyl]butanoate (16.71 mmole), tripropylamine (9.5 mL, 50.13 mmole), and xylenes (170 mL) was heated at reflux. After 63 hr the reaction was concentrated, and the residue was chromatographed on silica (2:1 EtOAc/hexanes, load with CH2Cl2). The title compound (5.33 g, 92% for two steps) was obtained as a light yellow solid: TLC (40% EtOAc/hexanes) Rf 0.49; 1H NMR (250, CDCl3) δ 7.04 (d, J=8.5 Hz, 1 H), 6.80 (dd, J=8.5, 2.6 Hz, 1 H), 6.61 (d, J=2.6 Hz, 1 H), 5.35 (d, J=16.8 Hz, 1 H), 3.60-4.30 (m, 4 H), 3.79 (s, 3 H), 3.71 (s, 3 H), 2.81-3.15 (m, 3 H), 2.46 (dd, J=16.9, 5.5 Hz, 1 H); MS (ES) m/e 368 (M+Na)+, 346 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. concentrationAfter 63 hr the reaction was concentrated
  4. customthe residue was chromatographed on silica (2:1 EtOAc/hexanes, load with CH2Cl2)

Sources & evidence

ORD record
ord-335081a7bfca4dda924e6065c5a58c49
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

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