Piperazine → 1-[(Naphthalen-1-yl)methyl]piperazine

HRID 1406661Notes

Reaction equation

HRID 1406661 reaction equation
Cl[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.[NH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>C1COCC1>[C:3]1([CH2:2][N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 68451-Chloromethylnaphthalene

Product 1

HCID 7018911-[(Naphthalen-1-yl)methyl]piperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Synthesized according to General Procedure A: 1-(chloromethyl)naphthalene (4{24}, 5 mL, 33.4 mmol, 1 equiv.), piperazine (17.3 g, 200.6 mmol, 6 equiv.), THF (73.0 mL). Purification with flash column chromatography on silica gel (4:1 EtOAc:MeOH) afforded 5{24} (6.58 g, 87%) as a beige solid. 1H-NMR (500 MHz, CDCl3): δ 8.32 (d, 1H, J=8.0 Hz), 7.85 (d, 1H, J=8.0 Hz), 7.78 (d, 1H, J=8.0 Hz), 7.54-7.47 (m, 2H), 7.44-7.39 (m, 2H), 3.89 (s, 2H), 2.87 (t, 4H, J=5.0 Hz), 2.48 (br s, 4H), 1.68 (br s, 1H). 13C-NMR (125 MHz, CDCl3): δ 134.3, 134.1, 132.8, 128.6, 128.1, 127.6, 125.9, 125.8, 125.3, 125.0, 62.0, 55.0, 46.4.

Workup

  1. customSynthesized
  2. customPurification with flash column chromatography on silica gel (4:1 EtOAc:MeOH)
  3. customafforded 5{24} (6.58 g, 87%) as a beige solid

Sources & evidence

ORD record
ord-bcc87bddbcbb47698220ff96d82fff4a
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

Loading…