Dichloromethane → Ammonia dichloromethane

HRID 456959

반응식

HRID 456959 반응식
[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:19]1([CH:25]=[CH:26][CH2:27][N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].[CH2:50]([Cl:52])[Cl:51]>C(O)(=O)C>[NH3:1].[CH2:50]([Cl:52])[Cl:51].[C:19]1([CH:25]=[CH:26][CH2:27][N:28]2[CH2:29][CH2:30][N:31]([CH2:15][C:14]3[CH:17]=[CH:18][C:11]([O:10][CH2:9][CH2:8][CH2:7][N:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)=[CH:12][CH:13]=3)[CH2:32][CH2:33]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

8

반응물 5

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 86803CinnamylpiperazineHCID 27663244-(3-Piperidin-1-ylpropoxy)benzaldehydeHCID 5049666Sodium triacetoxyborohydride

생성물 2

HCID 22731429Ammonia dichloromethane수율 1%HCID 687003271-(3-Phenyl-allyl)-4-[4-(3-piperidin-1-yl-propoxy)-benzyl]-piperazine

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A solution of the product of Example 9 (215 mg), 1-(3-phenyl-allyl)-piperazine (176 mg), and acetic acid (0.06 mL) in DCM (3 mL) was treated with sodium triacetoxyborohydride (290 mg). After 16 h, the resulting mixture was treated with 10% sodium hydroxide (5 mL) and extracted with DCM (3×10 mL). The combined organic phases were dried (sodium sulfate) and evaporated. Chromatography of the residue (1–5% 2 M methanolic ammonia/DCM) gave the title compound as a colorless oil (303 mg). 1H NMR (400 MHz, CDCl3): 7.36 (m, 2H), 7.30 (m, 2H), 7.24–7.18 (m, 3H), 6.83 (d, J=8.6 Hz, 2H), 6.51 (d, J=15.9 Hz, 1H), 6.31–6.23 (m, 1H), 3.98 (t, J=6.3 Hz, 2H), 3.45 (s, 2H), 3.15 (m, 2H), 2.60–2.32 (m, 12H), 1.67 (br, 1H), 1.62–1.56 (m, 4H), 1.47–1.40 (m, 2H).

후처리

  1. extractionextracted with DCM (3×10 mL)
  2. dry with materialThe combined organic phases were dried (sodium sulfate)
  3. customevaporated

출처 및 근거

ORD 기록
ord-5561b61465704a789ecf559db8adeca0
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07186732B2

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