Triethylamine → HCID 178456388, compound

HRID 1984023Notes

Reaction equation

HRID 1984023 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:10])=O)[CH2:4][CH2:3]1.[CH:11]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)([CH3:13])[CH3:12].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[CH:11]([N:14]1[CH2:19][CH2:18][N:17]([C:8]([C@H:5]2[CH2:4][CH2:3][C@H:2]([OH:1])[CH2:7][CH2:6]2)=[O:10])[CH2:16][CH2:15]1)([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 780131-IsopropylpiperazineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178525780HCID 178525780, compound

Product 1

HCID 178456388HCID 178456388, compoundYield 51.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1 g (6.9 mmol) of trans-4-hydroxycyclohexanecarboxylic acid (commercially available), 1.07 mg (8.3 mmol) of 1-(isopropyl)-piperazine (commercially available), 2.67 g (8.3 mmol) of TBTU and 1.54 g (15.2 mmol) of triethylamine in 7 ml DMF was stirred for 12 h at room temperature. The mixture was diluted with AcOEt, washed with water and brine, dried over MgSO4, and evaporated. The mixture was purified by column chromatography on NH2-silicagel eluting with CH2Cl2 and methanol=from 100:0 to 98:2. Evaporation of the combined product fractions yielded 0.9 g (51%) of the title compound as brown oil. MS (m/e): 255.2 (MH+).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe mixture was purified by column chromatography on NH2-silicagel eluting with CH2Cl2 and methanol=from 100:0 to 98:2
  5. customEvaporation of the combined product fractions

Sources & evidence

ORD record
ord-ca476d1ead7140958da7da0040eaa9b5
Source dataset
uspto-grants-2009_06
Patent number
US07544683B2

Reaction notes

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