Triethylamine → Methyl 6-[2-(3,5-dimethylphenoxy)acetylamino]hexanoate

HRID 1593258Notes

Reaction equation

HRID 1593258 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:13][C:14]1[CH:15]=[C:16]([CH:22]=[C:23]([CH3:25])[CH:24]=1)[O:17][CH2:18][C:19]([OH:21])=O.C(N(CC)CC)C.Cl.[NH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][C:40]([O:42][CH3:43])=[O:41]>ClCCl>[CH3:25][C:23]1[CH:22]=[C:16]([CH:15]=[C:14]([CH3:13])[CH:24]=1)[O:17][CH2:18][C:19]([NH:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][C:40]([O:42][CH3:43])=[O:41])=[O:21]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 794053,5-Xylyloxyacetic acidHCID 11499324Methyl 6-aminohexanoate hydrochloride

Product 1

HCID 58999252Methyl 6-[2-(3,5-dimethylphenoxy)acetylamino]hexanoateYield 62.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

In a 5L 3-necked flask equipped with a mechanical stirrer and a dropping funnel was placed 1,1′-carbonyldiimidazole (94.4 g, 0.583 mol) in dichloromethane (1 L). A solution of 3,5-dimethylphenoxyacetic acid (Intermediate A77, 95.4 g, 0.53 mol) in dichloromethane (1250 mL) was added over a period of 60 min under argon. Triethylamine (107.1 g, 1.06 mol) was added followed by addition of a suspension of methyl 6-aminohexanoate hydrochloride (101.1 g, 0.555 mol) in dichloromethane (250 mL) in five portions. After 1 hr the reaction mixture was washed with 3 M HCl (1×1L), 2 M ammonium hydroxide (1×1L), and water (1×1L). The organic phase was then filtered through 1PS filter paper and concentrated under reduced pressure to give an oil. Distillation of the oil gave 101.5 g (62%) of the title compound, amide boiling at 197-202° C. (1 mm). The oil solidified on standing.

Workup

  1. washAfter 1 hr the reaction mixture was washed with 3 M HCl (1×1L), 2 M ammonium hydroxide (1×1L), and water (1×1L)
  2. filtrationThe organic phase was then filtered through 1PS filter paper
  3. concentrationconcentrated under reduced pressure
  4. customto give an oil
  5. distillationDistillation of the oil

Sources & evidence

ORD record
ord-64be88e7c7d64c4daacfde3cb86d6f0c
Source dataset
uspto-grants-2007_11
Patent number
US07294716B2

Reaction notes

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