Potassium Carbonate → 2-(2-(2-(Aminomethyl)-4-(dibenzo[b,f][1,4]thiazepin-11-yl)piperazin-1-yl)ethoxy)ethanol

HRID 625178Notes

Reaction equation

HRID 625178 reaction equation
[CH:1]1[C:6]2[C:7]([N:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][O:24][CH2:25][CH2:26][OH:27])[CH:18]([CH2:28][NH:29]C(=O)C(F)(F)F)[CH2:17]3)=[N:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[S:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[NH2:29][CH2:28][CH:18]1[CH2:17][N:16]([C:7]2[C:6]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[S:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[N:8]=2)[CH2:21][CH2:20][N:19]1[CH2:22][CH2:23][O:24][CH2:25][CH2:26][OH:27]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86711152N-((4-(Dibenzo[b,f][1,4]thiazepin-11-yl)-1-(2-(2-hydroxyethoxy)ethyl)piperazin-2-yl)methyl)-2,2,2-trifluoroacetamide

Product 1

HCID 733310772-(2-(2-(Aminomethyl)-4-(dibenzo[b,f][1,4]thiazepin-11-yl)piperazin-1-yl)ethoxy)ethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-((4-(dibenzo[b,f][1,4]thiazepin-11-yl)-1-(2-(2-hydroxyethoxy)ethyl)piperazin-2-yl)methyl)-2,2,2-trifluoroacetamide, prepared as described in the previous step, (2.0 g) and aqueous potassium carbonate (5%) (15 mL) in methanol (20 mL) was stirred at room temperature for 18 hours and extracted with ethyl acetate. The organic layers were washed with saturated aqueous sodium chloride, dried over sodium sulfate, filtered, evaporated to give the crude product which was purified by column chromatography, and followed by prep-HPLC to provide the title compound as a yellow solid. ESI-MS (M+1): 413 calc. for C22H28N4O2S 412. 1H NMR: (CDCl3, 400 MHz): δ (ppm) 7.52-7.50 (m, 1H), 7.41-7.31 (m, 4H), 7.17-7.12 (m, 1H), 7.02-7.00 (m, 1H), 6.89-6.84 (m, 1H), 3.66-3.59 (m, 5H), 3.54-3.51 (m, 2H), 3.49-3.38 (m, 1H), 3.19-3.12 (m, 1H), 3.03-2.88 (m, 2H), 2.79-2.53 (m, 5H).

Workup

  1. customprepared
  2. extractionextracted with ethyl acetate
  3. washThe organic layers were washed with saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto give the crude product which
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-ee59b0c965614a5e916bf76d4d4668f6
Source dataset
uspto-grants-2016_04
Patent number
US09304126B2

Reaction notes

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