4-Methylmorpholine → HCID 86687857, compound

HRID 535905Notes

Reaction equation

HRID 535905 reaction equation
[C:1]([OH:7])(=O)[CH2:2][CH2:3][C:4]#[CH:5].CN1CCOCC1.ClC(OCC(C)C)=O.[NH:23]([CH2:27][CH2:28][OH:29])[CH2:24][CH2:25][OH:26]>C(Cl)Cl.CN(C=O)C>[OH:26][CH2:25][CH2:24][N:23]([CH2:27][CH2:28][OH:29])[C:1](=[O:7])[CH2:2][CH2:3][C:4]#[CH:5]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 8113DiethanolamineHCID 224644-Pentynoic acidHCID 62365Isobutyl chloroformate

Product 1

HCID 86687857HCID 86687857, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-5 °C

Procedure

A mixture of 4-pentynoic acid (2.00 g; 20.4 mmol) and 4-methylmorpholine (2.24 ml; 20.4 mmol) in DCM (20 ml) is cooled to −5° C. Isobutyl chloroformate (2.68 ml; 20.4 mmol) is added, followed by DMF (10 ml). The resulting mixture is added in portions to a solution of diethanolamine (2.25 g; 21.4 mmol) in DCM (10 ml). The resulting mixture is stirred overnight and evaporated. The residue is purified by silica gel column chromatography (gradient: DCM/methanol 100:0→82:18 to yield N,N-bis(2-hydroxyethyl)pent-4-ynamide.

Workup

  1. customevaporated
  2. customThe residue is purified by silica gel column chromatography (gradient

Sources & evidence

ORD record
ord-d959d50e3fa54214bf28b2e898576f9f
Source dataset
uspto-grants-2014_10
Patent number
US08859559B2

Reaction notes

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