Triethylamine → HCID 15592117, compound

HRID 2417600Notes

Reaction equation

HRID 2417600 reaction equation
[O:1]=[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=[C:3]1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][OH:17])[CH2:11][CH2:10]1.C(N(CC)CC)C.[CH3:25][C:26]([CH3:31])([CH3:30])[C:27](Cl)=[O:28]>C(Cl)Cl>[CH3:25][C:26]([CH3:31])([CH3:30])[C:27]([O:17][CH2:16][CH2:15][N:12]1[CH2:11][CH2:10][N:9]([C:3]2[C:2](=[O:1])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:14][CH2:13]1)=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 155921092-[4-(2-Hydroxyethyl)piperazin-1-yl]cyclohepta-2,4,6-trien-1-one

Product 1

HCID 15592117HCID 15592117, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-oxo-3,5,7-cycloheptatrien-1-yl)-1-piperazine-ethanol (7.04 g, described in Example 7) in methylene chloride (100 ml), triethylamine (4.3 g) was added followed by the dropwise addition of 2,2-dimethylpropanoyl chloride. The resulting solution was allowed to stay at room temperature for 3 days, then washed with water, dried over sodium sulfate and evaporated. The residue was chromatographed twice on 250 g of silica gel with ethyl acetate to yield 3.5 g of the title compound. The title compound (3.0 g) was dissolved in acetone (15 ml) and a solution of maleic acid (1.16 g) in acetone (15 ml) was added. Diethyl ether (100 ml) was added to give the (Z)-2-butenedioate salt (2.5 g) of the title compound; mp 101°-102° C.; ir(mull) 2350, 1723, 1700 and 1545 cm-1 ; uv max(MeOH) 343 (ε=8040) and 251 nm(ε=12645); nmr(DMSO-d6 ) δ1.2 (m, 9H), 3.3 (m, 10H), 4.3 (m, 2H), 6.1 (s, 2H) and 6.95 (m, 5H); and Anal. Calcd for C18H26N2O3.C4H4O4 : C, 60.82% H, 6.96% N, 6.45% and Found: C, 60.74% H, 7.01% N, 6.16%.

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. customevaporated
  4. customThe residue was chromatographed twice on 250 g of silica gel with ethyl acetate

Sources & evidence

ORD record
ord-799b823d0a4947ae9ec41a4bb5e9277e
Source dataset
uspto-grants-1984_09
Patent number
US04469693

Reaction notes

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