4-Methoxyphenylacetic Acid → HCID 3296345, compound

HRID 1823829Notes

Reaction equation

HRID 1823829 reaction equation
Cl.CN(C)CCCN=C=NCC.[CH2:13]([N:20]1[CH2:25][CH2:24][CH:23]([NH2:26])[CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][C:36](O)=[O:37])=[CH:31][CH:30]=1.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>ClCCl>[CH2:13]([N:20]1[CH2:25][CH2:24][CH:23]([NH:26][C:36](=[O:37])[CH2:35][C:32]2[CH:33]=[CH:34][C:29]([O:28][CH3:27])=[CH:30][CH:31]=2)[CH2:22][CH2:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 5

HCID 76904-Methoxyphenylacetic AcidHCID 8471TriethylamineHCID 4158521-Benzyl-4-piperidylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 3296345HCID 3296345, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.42 g, 12.6 mmol) was added to a solution of 1-benzyl-4-piperidinamine (2.0 g, 10.5 mmol), 4-methoxyphenylacetic acid (1.83 g, 11.0 mmol), 1-hydroxybenzotriazole hydrate (1.56 g, 11.5 mmol) and triethylamine (2.70 ml, 26.2 mmol) in dichloromethane (100 ml). The reaction mixture was stirred for 18 hours after which time the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate and washed with water (3×), dried (MgSO4), filtered and the solvent removed under reduced pressure to afford the title compound as a white solid, 3.44 g.

Workup

  1. customwas evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water (3×)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-4ad66c689ea14a1ba40a3328d498d8eb
Source dataset
uspto-grants-2006_05
Patent number
US07041667B1

Reaction notes

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