4-(Trifluoromethyl)benzylamine → HCID 22458245, compound

HRID 2185554Notes

Reaction equation

HRID 2185554 reaction equation
[C:1]([CH2:4][CH:5]1[CH2:10][CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7][CH2:6]1)([OH:3])=O.[ClH:18].CN(CCCN=C=NCC)C.[F:30][C:31]([F:41])([F:40])[C:32]1[CH:39]=[CH:38][C:35]([CH2:36][NH2:37])=[CH:34][CH:33]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[ClH:18].[F:30][C:31]([F:40])([F:41])[C:32]1[CH:39]=[CH:38][C:35]([CH2:36][NH:37][C:1]([CH2:4][CH:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]2)=[O:3])=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 768044-(Trifluoromethyl)benzylamineHCID 1512539[1-(tert-Butoxycarbonyl)piperidin-4-yl]acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 22458245HCID 22458245, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

4-Carboxymethyl-1-tert-butoxycarbonylpiperidine (207 mg, 0.85 mmol, commercially available from Neosystem), 1-(3-(N,N-dimethylamino)-prop-1-yl)-3-ethylcarbodiimide hydrochloride (EDC) (177 mg, 0.92 mmol) and 4-(N,N-dimethylamino)pyridine (2 mg, 0.02 mmol) were dissolved in 4 mL of CH2Cl2. (4-(Trifluoromethyl)benzyl)amine (0.114 mL, 0.8 mmol) was added and the reaction was stirred at rt for 14 h. The mixture was diluted with CH2Cl2, washed with 1 N NaOH, 1 N HCl and brine and dried over MgSO4. The solvent was removed, the residue was redissolved in 1% HCl/methanol and the solution was heated to 50° C. for 24 h. The solution was then concentrated to afford 208 mg (77%) of the title compound. ESI-MS: 301.1 (M+H); HPLC A: 1.66 min.

Workup

  1. washwashed with 1 N NaOH, 1 N HCl and brine
  2. dry with materialdried over MgSO4
  3. customThe solvent was removed
  4. dissolutionthe residue was redissolved in 1% HCl/methanol
  5. temperaturethe solution was heated to 50° C. for 24 h
  6. concentrationThe solution was then concentrated

Sources & evidence

ORD record
ord-8fb2f9e7351145078c4a202cb3f05cb0
Source dataset
uspto-grants-2002_06
Patent number
US06399619B1

Reaction notes

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