Bis(2-Methoxyethyl)amine → HCID 86695280, compound

HRID 524557Notes

Reaction equation

HRID 524557 reaction equation
[C:1]([OH:8])(=O)[CH2:2][CH2:3][CH2:4][C:5]#[CH:6].CCN=C=NCCCN(C)C.Cl.[CH3:21][O:22][CH2:23][CH2:24][NH:25][CH2:26][CH2:27][O:28][CH3:29]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:21][O:22][CH2:23][CH2:24][N:25]([CH2:26][CH2:27][O:28][CH3:29])[C:1](=[O:8])[CH2:2][CH2:3][CH2:4][C:5]#[CH:6]

Participants

6

Reactant 3

HCID 2383Bis(2-Methoxyethyl)amineHCID 1430365-Hexynoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 86695280HCID 86695280, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of hex-5-ynoic acid (7.11 g, 63.4 mmol), EDC.HCl (14.0 g, 72.9 mmol) and DMAP (387 mg, 3.17 mmol) in DCM (600 mL) at 0° C. was added bis(2-methoxyethyl)amine (9.3 mL, 63 mmol). The resulting mixture was warmed to RT for 20 hr and was then washed with hydrochloric acid (1 M, 2×500 mL) and water (500 mL). The organic layer was dried and evaporated in vacuo to afford the title compound, Intermediate B, as a yellow oil (16 g, 97%): 1H NMR (400 MHz, CDCl3) δ: 1.88 (3H, m), 2.26 (2H, m), 2.49 (2H, m), 3.32 (6H, s), 3.51 (4H, m), 3.55 (4H, m)

Workup

  1. washwas then washed with hydrochloric acid (1 M, 2×500 mL) and water (500 mL)
  2. customThe organic layer was dried
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-fea611f7a1da4a03bd46a8456df9a528
Source dataset
uspto-grants-2016_05
Patent number
US09340545B2

Reaction notes

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