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Dichloromethane → Ammonia dichloromethane

HRID 456963
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인쇄 미리보기

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HRID 456963 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.[CH2:19]([NH:26][CH3:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].[CH2:44]([Cl:46])[Cl:45]>C(O)(=O)C>[NH3:1].[CH2:44]([Cl:46])[Cl:45].[CH2:19]([N:26]([CH3:27])[CH2:15][C:14]1[CH:17]=[CH:18][C:11]([O:10][CH2:9][CH2:8][CH2:7][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:12][CH:13]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 6344DichloromethaneHCID 7669N-MethylbenzylamineHCID 14798Sodium HydroxideHCID 27663244-(3-Piperidin-1-ylpropoxy)benzaldehydeHCID 5049666Sodium triacetoxyborohydride

생성물 2

HCID 10291629Benzyl-methyl-[4-(3-piperidin-1-yl-propoxy)-benzyl]-amine
HCID 22731429
Ammonia dichloromethane
수율 1%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A solution of the product of Example 9 (218 mg), benzyl methylamine (108 mg), and acetic acid (0.05 mL) in DCM (3 mL) was treated with sodium triacetoxyborohydride (300 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 (269 mg). 1H NMR (400 MHz, CDCl3): 7.37–7.28 (m, 4H), 7.27–7.22 (m, 5H), 6.85 (d, J=8.6 Hz, 2H), 3.99 (t, J=6.3 Hz, 2H), 3.49 (s, 2H), 3.45 (s, 2H), 2.50–2.31 (m, 6H), 2.16 (s, 3H), 1.97 (m, 2H), 1.62–1.55 (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-e2d90f8310c24ac19df7e63738ec19c4
출처 데이터셋
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07186732B2

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