Triethylamine → HCID 59752913, 화합물

HRID 749997노트

반응식

HRID 749997 반응식
Cl.[Cl:2][C:3]1[CH:23]=[CH:22][C:6]([O:7][C:8]2[CH:21]=[CH:20][C:11]([O:12][CH2:13][C@@H:14]3[CH2:19][CH2:18][CH2:17][CH2:16][NH:15]3)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.Br[CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28].C(N(CC)CC)C>ClCCl.O>[CH3:30][O:29][C:27](=[O:28])[CH2:26][CH2:25][N:15]1[CH2:16][CH2:17][CH2:18][CH2:19][C@H:14]1[CH2:13][O:12][C:11]1[CH:20]=[CH:21][C:8]([O:7][C:6]2[CH:22]=[CH:23][C:3]([Cl:2])=[CH:4][CH:5]=2)=[CH:9][CH:10]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 76934Methyl 3-bromopropanoateHCID 68996119HCID 68996119, 화합물

생성물 1

HCID 59752913HCID 59752913, 화합물수율 25%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

A solution of (S)-2-[4-(4-chloro-phenoxy)-phenoxymethyl]-piperidine hydrochloride (218 mg, 0.615 mmol), methyl 3-bromopropionate (128 mg, 0.769 mmol), and triethylamine (124 mg, 1.23 mmol) in dichloromethane (2.5 mL) was heated for 18 h at 30° C. The mixture was diluted with 5 mls of water and extracted with dichloromethane (8 mL). The aqueous layer was re-extracted with ethyl acetate (8 mL). The combined organic layers were dried over anhy. Na2SO4 and the solvent was removed in vacuo to obtain the crude mixture, which was purified by silica gel flash chromatography to obtain the product (62 mg, 25%): 1H NMR (400 MHz, CDCl3); δ 1.48-1.77 (m, 6H), 2.22-2.36 (m, 1H), 2.52-2.57 (m, 2H), 2.68-2.71 (m, 1H), 2.84-2.97 (m, 2H), 3.09-3.16 (m, 1H), 3.66 (s, 3H), 3.91-3.94 (dd, 1H J1=4.4 Hz, J2=10.0 Hz), 4.02-4.06 (dd, 1H J1=5.2 Hz, J2=10.0 Hz), 6.86-6.96 (m, 5H), 7.23-7.26 (m, 3H)

후처리

  1. extractionextracted with dichloromethane (8 mL)
  2. extractionThe aqueous layer was re-extracted with ethyl acetate (8 mL)
  3. customThe combined organic layers were dried over anhy
  4. customNa2SO4 and the solvent was removed in vacuo
  5. customto obtain the crude mixture, which
  6. customwas purified by silica gel flash chromatography

출처 및 근거

ORD 기록
ord-dad3308e9b2543b790e56f457d8aae2f
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07402684B2

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