tert-Butyl piperazine-1-carboxylate → 4-[2-Hydroxy-3-[4-(tert-butoxycarbonyl)-1-piperazinyl]propoxy]benzylcyanide

HRID 1768951Notes

Reaction equation

HRID 1768951 reaction equation
[O:1]1[CH2:14][CH:2]1[CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:8]([CH2:9][C:10]#[N:11])=[CH:7][CH:6]=1.[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>CO>[OH:1][CH:2]([CH2:14][N:25]1[CH2:24][CH2:23][N:22]([C:20]([O:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:21])[CH2:27][CH2:26]1)[CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:8]([CH2:9][C:10]#[N:11])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 49623844-(2-Oxiranylmethoxy)benzeneacetonitrile

Product 1

HCID 189462924-[2-Hydroxy-3-[4-(tert-butoxycarbonyl)-1-piperazinyl]propoxy]benzylcyanideYield 70.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-(2,3-epoxypropoxy)benzylcyanide (2.84 g, 15 mmol) and 1-(tert-butoxycarbonyl)piperazine (4.2 g, 22.5 mmol) in methanol (35 ml) was stirred at room temperature for 3 hours and the solvent was removed. The residue was dissolved in 200 ml of ethyl acetate, washed with water, dried over MgSO4 and concentrated. The obtained crude product was chromatographed on a silica gel column eluting with ethyl acetate. The obtained sticky material was triturated with hexane to give 3.95 g of the title compound, yield: 70.2%, mp. 98°-100° C.

Workup

  1. customthe solvent was removed
  2. dissolutionThe residue was dissolved in 200 ml of ethyl acetate
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe obtained crude product
  7. customwas chromatographed on a silica gel column
  8. washeluting with ethyl acetate
  9. customThe obtained sticky material was triturated with hexane

Sources & evidence

ORD record
ord-8f1389f2428f48ac93586b282599b75a
Source dataset
uspto-grants-1995_01
Patent number
US05380724

Reaction notes

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