Trifluoroacetic acid → HCID 58046573, compound

HRID 706357Notes

Reaction equation

HRID 706357 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[CH2:17][N:18]2[CH2:23][CH2:22][C:21](=[CH:24]OC)[CH2:20][CH2:19]2)=[CH:11][CH:10]=1.Cl.[C:28]1([CH3:36])[CH:33]=[CH:32][C:31]([NH:34]N)=[CH:30][CH:29]=1.C([SiH](CC)CC)C>C(Cl)(Cl)Cl>[CH3:36][C:28]1[CH:33]=[C:32]2[C:21]3([CH2:22][CH2:23][N:18]([CH2:17]/[CH:16]=[CH:15]/[C:12]4[CH:13]=[CH:14][C:9]([Cl:8])=[CH:10][CH:11]=4)[CH2:19][CH2:20]3)[CH2:24][NH:34][C:31]2=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 125044-Methylphenylhydrazine monohydrochlorideHCID 58641837HCID 58641837, compound

Product 1

HCID 58046573HCID 58046573, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

Trifluoroacetic acid (0.75 ml) was added to a stirred solution of 1-[trans-3-(4-chlorophenyl)allyl]-4-methoxymethylenepiperidine- and 4-tolylhydrazine hydrochloride (28 mg) in chloroform (5 ml) and the reaction was heated to 50° C. for 5 h. Triethylsilane (2 ml) was added and the reaction was heated at 50° C. for a further 5 h. The mixture was allowed to cool and was quenched in concentrated ammonia solution/ice chips (20 ml). The aqueous phase was extracted twice with chloroform and the combined organics were dried over anhydrous magnesium sulphate and concentrated in vacuo to yield 0.04 g (63%) of the desired indoline. 1H NMR (400 MHz, CDCl3) 1.75 (d, J=9 Hz, 2H), 1.96 (td, J=8 & 2, 2H), 2.13 (t, J=9 Hz, 2H), 2.25 (s, 3H), 2.95 (d, J=10 Hz, 2H), 3.19 (d, J=5 Hz, 2H), 3.42 (s, 2H), 6.30 (dt, J=11 & 5 Hz, 1H), 6.48 (d, J=11 Hz, 1H), 6.58 (d, J=7 Hz, 1H), 6.85 (d, J=7 Hz, 1H), 6.9 (s, 1H), 7.30 (m, 4H). MS (ES+) 353/355 (M+H+), 203 (M-4-chlorocinnamyl+H+).

Workup

  1. temperaturethe reaction was heated at 50° C. for a further 5 h
  2. temperatureto cool
  3. customwas quenched in concentrated ammonia solution/ice chips (20 ml)
  4. extractionThe aqueous phase was extracted twice with chloroform
  5. dry with materialthe combined organics were dried over anhydrous magnesium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2f63515da8f64a83b29e4a7e53ddc469
Source dataset
uspto-grants-2015_11
Patent number
US09174987B2

Reaction notes

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