Ammonium Hydroxide → 2-(7-Trifluoromethyl-1H-indol-3-yl)-ethylamine

HRID 1666894ノート

反応式

HRID 1666894 の反応式
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9]N.CO[CH:15](OC)[CH2:16][CH2:17][CH2:18][NH2:19].[OH-].[NH4+]>Cl>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:4]=1[NH:9][CH:15]=[C:16]2[CH2:17][CH2:18][NH2:19]

参加物

5

反応物 3

HCID 14923Ammonium HydroxideHCID 5208002-(Trifluoromethyl)phenylhydrazineHCID 54638031-Butanamine, 4,4-dimethoxy-

生成物 1

HCID 210714292-(7-Trifluoromethyl-1H-indol-3-yl)-ethylamine

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

反応条件

温度
100 °C

実験手順

Combine in a 500 mL round bottom flask equipped with magnetic stirring, (2-trifluoromethyl-phenyl)-hydrazine (5.0 g, 28.4 mmol) and 4-aminobutyraldehyde dimethyl acetal (4.54 g, 34.1 mmol) and stir. After 5 minutes, slowly add 1N HCl (200 mL) and heat the reaction to 85° C. for 2 hours forming an orange-red colored solution. Increase the temperature to 100° C. for 10 minutes and cool to room temperature. Pour the reaction mixture over ice and stir for 10 minutes followed by adjustment to pH ˜10 with ammonium hydroxide. Extract the mixture with methylene chloride, pool the organic phases, dry over sodium sulfate, and concentrate in vacuo to give a dark orange-brown oil. Purification on a pre-packed, HMDS treated silica column using a step gradient of 9% to 17% methanol in methylene chloride gives the pure title compound as an orange oil: 1H NMR (400 MHz, dmso-d6): 11.18 (br s, 1H), 7.82 (d, 1H, J=7.6 Hz), 7.40 (d, 1H, J=7.2 Hz), 7.24 (d, 1H, J=2.0 Hz), 7.13 (t, 1H, J=7.6 Hz) 2.76-2.83 (m, 4H). MS (APCI): m/e 229.0 (M+1), 212.0 (M−NH2).

後処理

  1. customthe reaction to 85° C. for 2 hours
  2. customforming an orange-red colored solution
  3. temperaturecool to room temperature
  4. additionPour the reaction mixture over ice
  5. stirringstir for 10 minutes
  6. extractionExtract the mixture with methylene chloride, pool the organic phases
  7. dry with materialdry over sodium sulfate
  8. concentrationconcentrate in vacuo
  9. customto give a dark orange-brown oil
  10. customPurification on a pre-packed, HMDS
  11. additiontreated silica column

出典と根拠

ORDレコード
ord-8882850398af46b2b44cdef92239a268
出典データセット
uspto-grants-2011_10
特許番号
US08044090B2

反応ノート

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