4-Methylmorpholine → HCID 87901234, compound

HRID 1796860Notes

Reaction equation

HRID 1796860 reaction equation
[CH3:1][CH:2]([CH3:12])[CH2:3][CH2:4][C@@H:5]([CH2:9][CH:10]=[CH2:11])[C:6](O)=[O:7].Cl.[CH3:14][NH:15][O:16][CH3:17].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>ClCCl>[CH3:17][O:16][N:15]([CH3:14])[C:6](=[O:7])[C@@H:5]([CH2:4][CH2:3][CH:2]([CH3:12])[CH3:1])[CH2:9][CH:10]=[CH2:11]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 87901224HCID 87901224, compound

Product 1

HCID 87901234HCID 87901234, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of Example 8D (4.54 g, 26.7 mmol), N,O-dimethyl hydroxylamine hydrochloride (5.6 g, 57 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (5.19 g, 27 mmol), 1-hydroxybenzotriazole (4.12 g, 30.5 mmol), and N-methylmorpholine (7.0 mL, 64 mmol) in dichloromethane (270 mL) at room temperature was stirred for 4 hours, diluted with dichloromethane, washed sequentially with aqueous NaHCO3, brine, 10% KHSO4, and brine, dried (MgSO4), filtered, and concentrated. Flash column chromatography (silica gel, 10% ethyl acetate/hexanes) provided the desired product. MS (ESI(+)) m/e 214 (M+H)+.

Workup

  1. washwashed sequentially with aqueous NaHCO3, brine, 10% KHSO4, and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2c6d89360b9742f088bdd9f6d7a9b235
Source dataset
uspto-grants-2006_04
Patent number
US07030262B2

Reaction notes

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