Triethylamine → HCID 59382077, compound

HRID 2196048Notes

Reaction equation

[O:1]([CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]1[O:20][C:19]2[CH:21]=[C:22]([Cl:27])[C:23]([CH2:25]Cl)=[CH:24][C:18]=2[O:17]1.CCN(CC)CC>O1CCCC1>[Cl:27][C:22]1[C:23]([CH2:25][N:13]2[CH2:12][CH2:11][N:10]([CH2:9][CH2:8][O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:15][CH2:14]2)=[CH:24][C:18]2[O:17][CH2:16][O:20][C:19]=2[CH:21]=1

Participants

Conditions

Temperature: 60 °C

Procedure

1-[2-(phenoxy)-ethyl]piperazine (200 mg, 0.974 mmol), 6-chloropiperonyl chloride (200 mg, 0.974 mmol), and Et3N (415 μL, 3 mmol) were combined in tetrahydrofuran (THF 20 mL). The reaction mixture was heated at 60° C. for 12 h. The reaction mixture was cooled and extracted with ethyl acetate (EtOAc). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and evaporated. The crude residue was chromatographed on silica (20% EtOAc/Hexanes) and the product fractions were collected and evaporated to an amber solid (186 mg, 51%). 1H NMR (CDCl3) δ: 2.5-2.7 (m, 8H), 2.8 (t, 2H), 3.5 (s, 2H), 4.1 (t, 2H), 5.9 (s, 2H), 6.81 (s, 1H), 6.9-6.94 (m, 3H), 6.96-6.98 (m, 1H), 7.26-7.3 (m, 1H). MS ELS+ 376. CHN: calc., 64.08, 6.18, 7.47; found, 63.87, 6.12, 7.44. mp: 72-76° C.

Workup

temperatureThe reaction mixture was cooled
extractionextracted with ethyl acetate (EtOAc)
washThe combined organic layers were washed with brine
dry with materialdried over anhydrous Na2SO4
customevaporated
customThe crude residue was chromatographed on silica (20% EtOAc/Hexanes)
customthe product fractions were collected
customevaporated to an amber solid (186 mg, 51%)

Sources & evidence

ORD record: ord-0faf34bf351a44a8b201c3afe964d43d
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338430B2

Reaction notes

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