Triethylamine → HCID 65544462, compound

HRID 1020432Notes

Reaction equation

HRID 1020432 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9].C(N(CC)CC)C.C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C.[Br:43][C:44]1[C:45]([CH3:53])=[C:46]([CH:50]=[CH:51][CH:52]=1)[C:47](O)=[O:48]>C(Cl)Cl.C(OCC)(=O)C.CCCCCC>[Br:43][C:44]1[C:45]([CH3:53])=[C:46]([CH:50]=[CH:51][CH:52]=1)[C:47]([NH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9])=[O:48]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 27355903-Bromo-2-methylbenzoic AcidHCID 11499324Methyl 6-aminohexanoate hydrochloride

Product 1

HCID 65544462HCID 65544462, compoundYield 31.2%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.27 g of methyl 6-aminohexanoate hydrochloride (6.98 mmol) was dissolved in 25 ml of CH2Cl2 with stirring. 941 mg of triethylamine (9.3 mmol, 1.3 ml) was added to the mixture, and dicyclohexylcarbodiimide (DCC; 1.15 g, 5.58 mmol), dimethylaminopyridine (DMAP; 56.8 mg, 10 mol %), and 3-bromo-2-methylbenzoic acid (1.00 g, 4.65 mmol) was added thereto and stirred under a nitrogen atmosphere. After 24 hrs, the resulting mixture was subjected to thin layer chromatography to monitor the amount of the starting materials consumed, and the reaction was terminated by adding H2O thereto and extracted with CH2Cl2. The separated organic layer was dried over MgSO4 and removed the solvent under a reduced pressure. The residue thus obtained was subjected to a column chromatography (hexane:ethyl acetate=1:1, v/v) to obtain the title compound (497 mg, 31%).

Workup

  1. additionwas added
  2. stirringstirred under a nitrogen atmosphere
  3. customconsumed
  4. customthe reaction was terminated
  5. additionby adding H2O
  6. extractionextracted with CH2Cl2
  7. dry with materialThe separated organic layer was dried over MgSO4
  8. customremoved the solvent under a reduced pressure
  9. customThe residue thus obtained

Sources & evidence

ORD record
ord-bc22fc382ae84e2eb1f6ac1cead07909
Source dataset
uspto-grants-2014_05
Patent number
US08716326B2

Reaction notes

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