Piperidine → HCID 18426242, compound

HRID 133621Notes

Reaction equation

HRID 133621 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N=C=NC(C)C)(C)C.O.ON1C2C=CC=CC=2N=N1.[C:27]([C:30]1[CH:60]=[CH:59][C:33]([CH2:34][N:35]2[CH2:40][CH2:39][CH:38]([CH2:41][NH:42][C:43](=[O:58])[CH2:44][NH:45][C:46](=[O:57])[C:47]3[CH:52]=[CH:51][CH:50]=[C:49]([C:53]([F:56])([F:55])[F:54])[CH:48]=3)[CH2:37][CH2:36]2)=[CH:32][CH:31]=1)(O)=[O:28]>CN(C=O)C>[N:1]1([C:27]([C:30]2[CH:60]=[CH:59][C:33]([CH2:34][N:35]3[CH2:40][CH2:39][CH:38]([CH2:41][NH:42][C:43](=[O:58])[CH2:44][NH:45][C:46](=[O:57])[C:47]4[CH:52]=[CH:51][CH:50]=[C:49]([C:53]([F:54])([F:56])[F:55])[CH:48]=4)[CH2:37][CH2:36]3)=[CH:32][CH:31]=2)=[O:28])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 12734DiisopropylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 18426279HCID 18426279, compound

Product 1

HCID 18426242HCID 18426242, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Piperidine (0.048 mg), and a DMF (0.15 mL) solution of diisopropylcarbodiimide (0.45 mmol) and 1-hydroxybenzotriazole hydrate (0.45 mmol) were added to a DMF (1.0 mL) solution of 1-(4-carboxybenzyl)-4-[[N-(3-(trifluoromethyl)benzoyl)glycyl]aminomethyl]piperidine (0.040 mmol), and the resulting mixture was shaken at room temperature for 17 hours, then loaded onto a Varian™ SCX column and washed with chloroform/methanol=1:1 (5 mL) and methanol (5 mL). The obtained crude product was eluted with a 2 M methanol solution of NH3 (5 mL) and concentrated to thereby provide 1-[4-(piperidinocarbonyl)benzyl]-4-[[N-(3-(trifluoromethyl)benzoyl)glycyl]aminomethyl]piperidine (Compd. No. 0.1572) (14.3 mg, 66%). The purity was determined by RPLC/MS (99%). ESI/MS m/e 545 (M++H, C29H35F3N4O3).

Workup

  1. washwashed with chloroform/methanol=1:1 (5 mL) and methanol (5 mL)
  2. customThe obtained crude product
  3. washwas eluted with a 2 M methanol solution of NH3 (5 mL)
  4. concentrationconcentrated to thereby provide 1-[4-(piperidinocarbonyl)benzyl]-4-[[N-(3-(trifluoromethyl)benzoyl)glycyl]aminomethyl]piperidine (Compd. No

Sources & evidence

ORD record
ord-e93326b1a23b4c0280eb8857c85b6baa
Source dataset
uspto-grants-2008_06
Patent number
US07390830B1

Reaction notes

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