1,2-Dichloroethane → Ammonia dichloromethane

HRID 33708노트

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HRID 33708 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.[ClH:19].[CH3:20][NH:21][CH3:22].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].ClC[CH2:41][Cl:42]>C(O)(=O)C>[NH3:1].[CH2:41]([Cl:42])[Cl:19].[CH3:20][N:21]([CH3:22])[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

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 10473Dimethylamine, hydrochlorideHCID 14798Sodium HydroxideHCID 27663244-(3-Piperidin-1-ylpropoxy)benzaldehydeHCID 5049666Sodium triacetoxyborohydride

생성물 2

HCID 9835304Dimethyl-[4-(3-piperidin-1-yl-propoxy)-benzyl]-amineHCID 22731429Ammonia dichloromethane수율 3%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A solution of the product of Example 9 (175 mg), dimethylamine hydrochloride (64 mg), and acetic acid (0.05 mL) in DCE (3 mL) was treated with sodium triacetoxyborohydride (210 mg). After 16 h, the resulting mixture was treated with 10% sodium hydroxide (1 mL) and extracted with DCM (3×3 mL). The combined organic phases were dried (magnesium sulfate) and evaporated. Chromatography of the residue (3% 2 M methanolic ammonia/DCM) gave the title compound as a colorless oil (70 mg). 1H NMR (400 MHz, CDCl3): 7.19 (d, J=8.6 Hz, 2H), 6.85 (d, J=8.6 Hz, 2H), 3.99 (t, J=6.4 Hz, 2H), 3.35 (s, 2H), 2.50-2.35 (m, 6H), 2.22 (s, 6H), 2.01-1.94 (m, 2H), 1.63-1.55 (m, 4H), 1.46-1.40 (m, 2H).

후처리

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

출처 및 근거

ORD 기록
ord-6997b950122f4a9b92b87a8a9051f427
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429586B2

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