Triethylamine → HCID 21109929, compound

HRID 1766187Notes

Reaction equation

HRID 1766187 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][C:7]([CH3:34])([O:9][C:10]([N:12]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[NH2:33])[CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][CH2:14]1)=[O:11])[CH3:8].C(N(CC)CC)C>O1CCCC1>[CH3:8][C:7]([CH3:34])([O:9][C:10]([N:12]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[NH:33][S:2]([CH3:1])(=[O:4])=[O:3])[CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:15][CH2:14]1)=[O:11])[CH3:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21109928HCID 21109928, compound

Product 1

HCID 21109929HCID 21109929, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.64 ml. (21 mmol) of methanesulphonyl chloride was added dropwise to a solution of 7.91 g (20 mmol) of N-(1,1-dimethylethoxycarbonyl)-N-[(2-aminophenyl)methyl]-1-(phenylmethyl)-4-piperidineamine and 3.0 ml (21 mmol) of triethylamine in 100 ml of tetrahydrofuran and the mixture was then kept for 12 hours at ambient temperature. It was then diluted with 100 ml of EE and extracted twice with 70 ml of saturated sodium hydrogen carbonate solution. The ethyl acetate phase was dried over sodium sulphate and concentrated by evaporation in vacuo. 8.7 g (92% of theoretical) of a colourless substance were obtained, Rf 0.85 (El D), which were used in the next step without any further purification.

Workup

  1. additionIt was then diluted with 100 ml of EE
  2. extractionextracted twice with 70 ml of saturated sodium hydrogen carbonate solution
  3. dry with materialThe ethyl acetate phase was dried over sodium sulphate
  4. concentrationconcentrated by evaporation in vacuo
  5. custom8.7 g (92% of theoretical) of a colourless substance were obtained
  6. customRf 0.85 (El D), which were used in the next step without any further purification

Sources & evidence

ORD record
ord-2276117a2a99496cbec32e38cdedf1cd
Source dataset
uspto-grants-2007_06
Patent number
US07230001B1

Reaction notes

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