Triethylamine → HCID 66651956, compound

HRID 418934Notes

Reaction equation

HRID 418934 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:25]([NH2:27])=O)[C:6]2[CH2:7][CH:8]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[CH:9]3[CH:14]([C:15]=2[CH:16]=1)[CH2:13][CH2:12][CH2:11][CH2:10]3.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:25]#[N:27])[C:6]2[CH2:7][CH:8]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[CH:9]3[CH:14]([C:15]=2[CH:16]=1)[CH2:13][CH2:12][CH2:11][CH2:10]3

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 66652109HCID 66652109, compound

Product 1

HCID 66651956HCID 66651956, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine 3-Methoxy-9-(4-methoxy-phenyl)-4b,5,6,7,8,8a,9,10-octahydro-phenanthrene-1-carboxylic acid amide (0.69 g, 0.19 mmol), and triethylamine (0.038 g, 0.38 mmol) in methylene chloride (2.5 ml) at 0-5° C. and add trifluoroacetic anhydride (0.044 g, 0.21 mmol). Let stir at r.t. for 15 minutes. Add water, separate organic layer. Dry over anhydrous sodium sulfate and remove solvent in vacuo to yield preparation 122 (0.066 g, 100%). 1H NMR (CDCl3): 7.24 (d, J=8.8 Hz, 2H), 7.22 (s, 1H), 7.06 (s, 1H), 6.94 (d, J=8.8, 2H), 3.86 (m, 6H), 3.2 (m, 4H), 2.5 (m, 1H), 2.1 (m, 1H), 1.8-0.8 (m, 7H).

Workup

  1. customAdd water, separate organic layer
  2. dry with materialDry over anhydrous sodium sulfate
  3. customremove solvent in vacuo
  4. customto yield

Sources & evidence

ORD record
ord-b603620529334d838ef445acb675c83c
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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