1,2-Dichloroethane → Ammonia dichloromethane

HRID 456948노트

반응식

HRID 456948 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-d72aa23dc6e241c0a8dccca700e25a1a
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07186732B2

반응 노트

불러오는 중…