Trifluoroacetic acid → 1-Benzyl-3-(naphthalen-2-ylmethyl)piperazine

HRID 10178

Reaction equation

HRID 10178 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH:9]1[CH2:21][C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=1)=O)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[NH4+]>ClCCl>[CH2:14]([N:11]1[CH2:12][CH2:13][NH:8][CH:9]([CH2:21][C:22]2[CH:31]=[CH:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=2)[CH2:10]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 210410814-Benzyl-2-(naphthalen-2-ylmethyl)piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 219788151-Benzyl-3-(naphthalen-2-ylmethyl)piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-benzyl-2-(naphthalen-2-ylmethyl)piperazine-1-carboxylic acid tert-butyl ester (0.75 g) in dichloromethane (3 mL) was added dropwise trifluoroacetic acid (3 mL). After 75 min at room temperature the mixture was poured onto ice and made basic by the addition of ammonium hydroxide (25% solution). The layers were separated and the aqueous layer extracted with dichloromethane. The combined organic layers were dried over magnesium sulphate, filtered, and concentrated in vacuo to afford 1-benzyl-3-(naphthalen-2-ylmethyl)piperazine as an oil; 053 g (93%) MH+ 317, Rf 0.61 (CH2Cl2/MeOH/NH4OH 93/7/0.5), which was used as such.

Workup

  1. additionAfter 75 min at room temperature the mixture was poured onto ice
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with dichloromethane
  4. dry with materialThe combined organic layers were dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dbc56614992c4ee4a364e93a778a758a
Source dataset
uspto-grants-2006_08
Patent number
US07094779B2

Linked notes

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