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

HRID 216103

反応式

HRID 216103 の反応式
[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

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 6882334-Trifluoromethoxy-(2-nitro-vinyl)-benzeneHCID 178418361HCID 178418361、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-757da75bae0446a7ac4103bb2adc5399
出典データセット
uspto-grants-2012_06
特許番号
US08193183B2

関連ノート

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