HCID 59470548, compound → HCID 59470555, compound

HRID 452305Notes

Reaction equation

HRID 452305 reaction equation
[F:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1>Cl.O1CCOCC1>[F:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:9][CH:10]=1

Participants

4

Reactant 1

HCID 59470548HCID 59470548, compound

Product 1

HCID 59470555HCID 59470555, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Tert-butyl 4-(4-(3-fluoropropyl)phenyl)piperazine-1-carboxylate (78 mg, 0.24 mmol) was dissolved in a 4.0M solution of HCl in dioxane (3 mL) and stirred at room temperature. After 1 h 1-(4-(3-fluoropropyl)phenyl)piperazine hydrochloride was collected as a white solid via filtration (63 mg). 1H NMR (300 MHz, CDCl3): δ 9.58 (br s, 2H), 9.38 (br s, 1H), 7.15 (d, 2H, J=8.7 Hz), 7.00 (d, 2H, J=8.6 Hz), 4.49 (t, 1H, J=6.0 Hz), 4.34 (t, 1H, J=6.0 Hz), 3.40 (dd, 4H, J=5.5, 4.7 Hz), 3.22 (br s, 4H), 2.59 (dd, 2H, J=8.1, 6.3 Hz), 1.98-1.80 (m, 2H); 19F NMR (282.4 MHz, CDCl3): δ−217.98 (m, 1F); 13C NMR (75.5 MHz, CDCl3): δ 147.3, 133.6, 128.9, 116.71, 83.6 (82.5), 46.2, 42.2, 31.5 (31.4), 29.7 (29.6); HRMS calcd for C13H19FN2:223.160503 found 223.16060.

Workup

  1. filtrationAfter 1 h 1-(4-(3-fluoropropyl)phenyl)piperazine hydrochloride was collected as a white solid via filtration (63 mg)

Sources & evidence

ORD record
ord-78d885bf94744853b35febd2d60e0540
Source dataset
uspto-grants-2013_07
Patent number
US08491868B2

Reaction notes

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