Sodium Carbonate → tert-Butyl 4-(bromoacetyl)piperazine-1-carboxylate

HRID 1241410Notes

Reaction equation

HRID 1241410 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].NC1N=CN=C([N:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)C=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[Br:1][CH2:2][C:3]([N:13]1[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]1)=[O:4]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 61147Bromoacetyl bromideHCID 21934614tert-Butyl 4-(6-aminopyrimidin-4-yl)piperazine-1-carboxylate

Product 1

HCID 15829155tert-Butyl 4-(bromoacetyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of bromoacetyl bromide (0.59 g, 2.95 mmol) in methylene chloride (3 mL) was added drop wise via addition funnel to a stirred solution of tert-butyl piperazine-1-carboxylate 12-1 (0.50 g, 2.68 mmol) and aqueous sodium carbonate (0.34 g, 3.22 mmol) in methylene chloride (15 mL) at 0° C. After a 10 minute reaction time the methylene chloride layer was drawn off, dried and evaporated to an oil. This was purified this on a silica column to afford 42-1. Hi-Res MS (M+Na): calc: 329.0471 found: 329.0462. 1H-NMR(CDCl3): 3.87(s, 2H); 3.61(m, 2H); 3.52(m, 2H); 3.50(m, 2H); 3.44(m, 2H); 1.47(s, 9H).

Workup

  1. customdried
  2. customevaporated to an oil
  3. customThis was purified this on a silica column
  4. customto afford 42-1

Sources & evidence

ORD record
ord-06e41ac235554e3a94252187fedbbc85
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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