Sodium Hydroxide → 2-[4-(2-Fluorophenyl)piperazin-1-yl]ethanamine

HRID 256474Notes

Reaction equation

HRID 256474 reaction equation
[C:1]([CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])[CH2:6][CH2:5]1)#[N:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C(OCC)C.O>[NH2:2][CH2:1][CH2:3][N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])[CH2:8][CH2:9]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 13959104HCID 13959104, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 110095812-[4-(2-Fluorophenyl)piperazin-1-yl]ethanamineYield 183.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 3283Diethyl EtherSolvent

Procedure

1-(Cyanomethyl)-4-(2-fluorophenyl)piperazine (9.0 g, 41.0 mmol) was added in portions to a suspension of LiAlH4 (2.34 g, 61.6 mmol) in diethyl ether (200 ml) over 1/2 hour. The mixture was heated to reflux for 5 hours. Water (3 ml) was slowly added to the mixture, followed by a 15% solution of sodium hydroxide in water (3 ml) and water (9 ml). The inorganic solids were removed by filtration, and the filtrate was dried over MgSO4. The solvent was removed in vacuo to give the product (16.76 g, 70% yield) as an amber oil which slowly crystallized to a colorless solid, mp 108°-112° C. IR (KBr) 1502 cm-1 ; mass spectrum m/z 224 (MH+); 1H NMR (CDCl3) δ1.38 (s, 2H, NH2), 2.33-3.23 (m, 12H, NCH2), 6.80-7.06 (m, 4 H, Ph-H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 5 hours
  3. customThe inorganic solids were removed by filtration
  4. dry with materialthe filtrate was dried over MgSO4
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-b858361f02e34e9394fd1b53aecf1aab
Source dataset
uspto-grants-1987_10
Patent number
US04703120

Reaction notes

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