Dichloromethane → HCID 21689652, compound

HRID 2210716Notes

Reaction equation

HRID 2210716 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[CH2:22]([CH:24]1[O:26][CH2:25]1)[Cl:23].C([O-])(O)=O.[Na+].C(Cl)Cl>C(O)C>[OH2:26].[Cl:23][CH2:22][CH:24]([OH:26])[CH2:25][N:19]1[CH2:18][CH2:17][N:16]([CH:8]([C:9]2[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=2)[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7835EpichlorohydrinHCID 1529321-(Bis(4-fluorophenyl)methyl)piperazineHCID 516892Sodium Bicarbonate

Product 1

HCID 21689652HCID 21689652, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

[Bis(4-fluorophenyl)methyl]piperazine, (14.4 g, 0.05 mol) in ethanol (200 mL) was added dropwise to epichlorohydrin (3.5 mL, 0.05 mol) in ethanol (12 mL) at 0° C. with NaHCO3 anhydrous (4.2 g, 0.05 mol) over 45 min under N2. The ice bath was removed and the mixture was allowed to come to room temperature. After 18 h the NaHCO3 was removed by fitration via a sintered glass funnel and the ethanol in the fitrate was removed in vacuo to give the crude product (21.3 g). Flash chromatography over silica gel using 2.0% methanol: methylene chloride gave pure product (10.05 g, 52.9%) as an amber oil. DCI/MS (M+1)381.400 MHz 1H NMR (CDCl3) δ: 7.3 (m,4H), 6.95 (m,4H), 4.2 (s, 1H), 3.95(m,1H),3.55(m,2H),2.7 (m,2H), 2.5(m,4M), 2.4 (m, 4H).

Workup

  1. customThe ice bath was removed
  2. customto come to room temperature
  3. customAfter 18 h the NaHCO3 was removed by fitration via a sintered glass funnel
  4. customthe ethanol in the fitrate was removed in vacuo
  5. customto give the crude product (21.3 g)

Sources & evidence

ORD record
ord-d2c43a16c0104237bfbb466caaeca969
Source dataset
uspto-grants-1995_10
Patent number
USRE035072

Reaction notes

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