Hydrochloric Acid → 2-[4-(Trifluoromethoxy)phenyl]ethan-1-amine hydrochloride

HRID 2110628

반응식

HRID 2110628 반응식
[F:1][C:2]([F:16])([F:15])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][N+:12]([O-])=O)=[CH:6][CH:5]=1.[H][H].[ClH:19]>CO.[Pd]>[ClH:19].[F:1][C:2]([F:15])([F:16])[O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][NH2:12])=[CH:8][CH:9]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 6882334-Trifluoromethoxy-(2-nitro-vinyl)-benzeneHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 429420892-[4-(Trifluoromethoxy)phenyl]ethan-1-amine hydrochloride수율 57%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A solution of 4-trifluoromethoxy benzaldehyde (1 g, 5.26 mmol) and nitromethane (0.96 g, 15.8 mmol) in acetic acid (10.6 mL) is treated with ammonium acetate (1.01 g, 13.2 mmol) is heated under microwave to 150° C. for 15 minutes. The reaction mixture is diluted with water, and extracted three times with DCM (50 mL). The combined extracts are washed sequentially with 2 N sodium hydroxide, water, and brine, dried over sodium sulfate and concentrated. The residue is subjected to silica gel chromatography to yield 4-trifluoromethoxy-(2-nitro-vinyl)-benzene (1.23 g) as a solid. A portion of 4-trifluoromethoxy-(2-nitro-vinyl)-benzene (0.504 g, 2.16 mmol) is hydrogenated with hydrogen in a balloon, 10% Pd/C (115 mg, 5 mol %) in MeOH (22 mL) containing concentrated hydrochloric acid (0.27 mL) at room temperature for 15 hours. The mixture is filtered and filtrate is concentrated to a solid that is washed with diethyl ether to obtain 2-(4-trifluoromethoxy-phenyl)-ethylamine hydrochloride [0.3 g, 57%, Intermediate (12)] as a solid. LC/MS: MS: 206 (M+H).

후처리

  1. filtrationThe mixture is filtered
  2. concentrationfiltrate is concentrated to a solid
  3. washthat is washed with diethyl ether

출처 및 근거

ORD 기록
ord-de8d9d61dfa7453b823e26836705c805
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07517889B2

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