1,1'-Carbonyldiimidazole → HCID 19926436, compound

HRID 1647086Notes

Reaction equation

HRID 1647086 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=O.[C:12]([N:19]1[CH:23]=[CH:22][N:21]=[CH:20]1)(N1C=CN=C1)=O.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1C1CNCCN1>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([N:19]1[CH2:23][CH2:22][N:21]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[O:25][CH3:24])[CH2:20][CH2:12]1)=[O:11]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 877542-Bromophenylacetic acidHCID 167407922-(2-Methoxyphenyl)piperazine

Product 1

HCID 19926436HCID 19926436, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

A stirred solution of 2-bromophenylacetic acid (28.4 g, 132 mmol) in chloroform (200 ml) was treated dropwise over 10 rain with 1,1'-carbonyldiimidazole (21.4 g, 132 mmol) in chloroform (120 ml) under argon, after 1 h treated with 2-(methoxyphenyl)piperazine (24.4 g, 127 mmol) in chloroform (100 ml), after 18 h washed with 0.5 N-HC1 (2×200 ml), 0.5 N-NaOH (2×200 ml), and brine (200 ml), dried (MgSO4), and evaporated in vacuo. The oil was crystallised by trituration with cyclohexane (100 ml) to give the product (27.0 g), m.p. 95°-97°.

Workup

  1. washwashed with 0.5 N-HC1 (2×200 ml), 0.5 N-NaOH (2×200 ml), and brine (200 ml)
  2. dry with materialdried (MgSO4)
  3. customevaporated in vacuo
  4. customThe oil was crystallised by trituration with cyclohexane (100 ml)

Sources & evidence

ORD record
ord-0c7f3e92b5e949319c817a7345c905b6
Source dataset
uspto-grants-1995_07
Patent number
US05430033

Reaction notes

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