2-(2,4-Dimethoxy-benzyl)-4-(3-morpholin-4-yl-propoxy)-2,3-dihydro-1H-isoindole → 4-(3-Morpholin-4-yl-propoxy)-2,3-dihydro-1H-isoindole

HRID 41418노트

반응식

HRID 41418 반응식
COC1C=C(OC)C=CC=1C[N:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[O:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH2:7]1>FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1.C(OCC)C.CO>[N:19]1([CH2:18][CH2:17][CH2:16][O:15][C:12]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:13]=2[CH2:14][NH:6][CH2:7]3)[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1

참가 물질

6

반응물 1

HCID 592631052-(2,4-Dimethoxy-benzyl)-4-(3-morpholin-4-yl-propoxy)-2,3-dihydro-1H-isoindole

생성물 1

HCID 469151864-(3-Morpholin-4-yl-propoxy)-2,3-dihydro-1H-isoindole수율 236.9%

시약·촉매·용매 4

HCID 887Methanol용매HCID 3283Diethyl Ether용매HCID 6422Trifluoroacetic acid용매HCID 7519Anisole용매

실험 절차

A solution of 2-(2,4-dimethoxy-benzyl)-4-(3-morpholin-4-yl-propoxy)-2,3-dihydro-1H-isoindole (233 mg, 0.56 mmol) in trifluoroacetic acid (1.0 mL) and anisole (0.5 mL) was heated at 150° C. under microwave irradiation for 10 minutes. The mixture was diluted with diethyl ether and extracted twice with water. The combined aqueous extracts were concentrated to give an oil which was dissolved in methanol and concentrated in vacuo to afford the title compound as a brown oil (348 mg, including residual TFA and/or water). 1H NMR (methanol-d4) 7.40 (1H, t), 7.03 (1H, d), 6.99 (1H, d), 4.63 (2H, s), 4.59 (2H, s), 4.21 (2H, t), 4.14-4.04 (2H, m), 3.85-3.73 (2H, m), 3.61-3.52 (2H, m), 3.41-3.36 (2H, m), 3.25-3.13 (2H, m), 2.32-2.25 (2H, m). MS: [M+H]+ 263.

후처리

  1. extractionextracted twice with water
  2. concentrationThe combined aqueous extracts were concentrated
  3. customto give an oil which
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-d949ecbfbf91462aa617e443fc057899
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530469B2

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