Morpholine → HCID 86669131, compound

HRID 400540Notes

Reaction equation

HRID 400540 reaction equation
[C:1]([OH:8])(=O)[CH2:2][CH2:3][CH2:4][C:5]#[CH:6].CCN=C=NCCCN(C)C.Cl.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[O:24]1[CH2:25][CH2:26][N:21]([C:1](=[O:8])[CH2:2][CH2:3][CH2:4][C:5]#[CH:6])[CH2:22][CH2:23]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 1430365-Hexynoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 86669131HCID 86669131, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of hex-5-ynoic acid (500 mg, 4.46 mmol), DMAP (27 mg, 0.23 mmol) and EDC hydrochloride (940 mg, 4.90 mmol) in DCM (10 mL) was added morpholine (391 μL, 4.46 mmol). The reaction was stirred at RT overnight and then diluted with DCM (50 mL). The resulting solution was washed with water (3×10 mL), brine (10 mL) and aq hydrochloric acid (2 M, 2×20 mL) and was then dried, filtered and evaporated in vacuo to afford the title compound (11) (808 mg, 100%) as a yellow oil: 1H NMR (500 MHz, CDCl3) δ: 3.65-3.71 (4H, m), 3.63 (2H, d), 3.45-3.54 (2H, m), 2.46 (2H, t), 2.26-2.33 (2H, m), 1.98 (1H, t), 1.88 (2H, quin).

Workup

  1. washThe resulting solution was washed with water (3×10 mL), brine (10 mL) and aq hydrochloric acid (2 M, 2×20 mL)
  2. customwas then dried
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-bf8150b09cc54d3fa39f443e13fd940c
Source dataset
uspto-grants-2014_06
Patent number
US08741909B2

Reaction notes

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