Diisopropylethylamine → 4-[4-(2-Fluoro-ethoxy)-phenyl]-piperazine-1-carboxamidine

HRID 452298Notes

Reaction equation

HRID 452298 reaction equation
[F:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1.C(N(C(C)C)CC)(C)C.[N:26]1([C:31](=N)[NH2:32])C=CC=N1>C(#N)C>[F:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:12][CH2:13][N:14]([C:31]([NH2:32])=[NH:26])[CH2:15][CH2:16]2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2734673PraxadineHCID 114922961-[4-(2-Fluoroethoxy)phenyl]piperazine

Product 1

HCID 594705454-[4-(2-Fluoro-ethoxy)-phenyl]-piperazine-1-carboxamidineYield 84.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(4-(2-fluoroethoxy)phenyl)piperazine (50 mg, 0.15 mmol) and diisopropylethylamine (59 μL, 0.34 mmol) in ACN (1 mL) was added 1H-pyrazole-1-carboximidamide (25 mg, 0.17 mmol). The reaction stirred at room temperature for 1 h, monitored by LC-MS. The precipitate was then filtered and washed with ACN to obtain the desired product as a white solid (33.8 mg, 58% yield). 1H NMR (300 MHz, DMSO-d6): δ 7.55 (br s, 3H), 6.95-6.86 (m, 4H), 4.78 (m, 1H), 4.62 (m, 1H), 4.21 (m, 1H), 4.11 (m, 1H), 3.57 (dd, 4H, J=5.2, 4.9 Hz), 3.09 (dd, 4H, J=5.1, 5.0 Hz); 19F NMR (DMSO-d6): δ−222.037 (m, 1F); 13C NMR (75.5 MHz, DMSO-d6): δ 156.0, 152.2, 144.9, 119.2, 115.1, 82.2 (81.1), 67.4 (67.2), 48.9, 44.9; HRMS calcd. for C12H17FN2O: 267.16157 found 267.16146.

Workup

  1. filtrationThe precipitate was then filtered
  2. washwashed with ACN

Sources & evidence

ORD record
ord-db2dd922ec5b45c8ba258717d9bc3572
Source dataset
uspto-grants-2013_07
Patent number
US08491868B2

Reaction notes

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