Sodium Iodide → HCID 68539905, compound

HRID 1441269Notes

Reaction equation

HRID 1441269 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][C@H:10]([CH3:14])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Br[CH2:16][C:17]([NH2:19])=[O:18].C(N(CC)C(C)C)(C)C.[I-].[Na+]>C(#N)C>[C:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:16][C:17]([NH2:19])=[O:18])[C@H:10]([CH3:14])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 696322-BromoacetamideHCID 81531DiisopropylethylamineHCID 2756811(R)-1-Boc-3-methylpiperazine

Product 1

HCID 68539905HCID 68539905, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (R)-1-Boc-3-methylpiperazine (100 mg, 0.50 mmol), 2-bromoacetamide (103 mg, 0.75 mmol), N,N-diisopropylethylamine (129 mg, 1.00 mmol) and sodium iodide (7.5 mg, 0.050 mmol) in acetonitrile (2.0 ml) was subjected to microwave irradiation at 100° C. for 5 minutes. The mixture was filtered through a 5 g Strata™ SCX giga tube, eluting with dichloromethane, methanol and then 2 M ammonia in methanol, and purified by flash chromatography eluting with ethyl acetate to 17% (v/v) methanol in ethyl acetate to afford (R)-2-(4-Boc-2-methylpiperazin-1-yl)acetamide (114 mg, 0.44 mmol).

Workup

  1. customirradiation at 100° C. for 5 minutes
  2. filtrationThe mixture was filtered through a 5 g Strata™ SCX giga tube
  3. washeluting with dichloromethane, methanol
  4. custom2 M ammonia in methanol, and purified by flash chromatography
  5. washeluting with ethyl acetate to 17% (v/v) methanol in ethyl acetate

Sources & evidence

ORD record
ord-216a366681bd41689e84123bfbfaf499
Source dataset
uspto-grants-2010_02
Patent number
US07655645B2

Reaction notes

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