6-Aminohexanoic Acid → ethyl 6-aminohexanoate hydrochloride

HRID 521281Notes

Reaction equation

HRID 521281 reaction equation
NCCCCCC(O)=O.S(Cl)([Cl:12])=O.Cl[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=[CH:17][C:16]=1[N+:25]([O-:27])=[O:26].Cl.[NH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36].C(N(CC)CC)C>ClCCl.C(O)C>[ClH:12].[NH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36].[N+:25]([C:16]1[CH:17]=[N:18][C:19]2[C:24]([C:15]=1[NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:23][CH:22]=[CH:21][CH:20]=2)([O-:27])=[O:26]

Participants

9

Reactant 5

HCID 5646-Aminohexanoic AcidHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 458476ethyl 6-aminohexanoate hydrochlorideHCID 112758084-Chloro-3-nitroquinoline

Product 2

HCID 458476ethyl 6-aminohexanoate hydrochlorideHCID 57447021HCID 57447021, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

Ethyl 6-aminocaproate hydrochloride was prepared from 6-aminocaproic acid, thionyl chloride, and ethanol by the general method of C. Temple, Jr., R. D. Elliott, and J. A. Montgomery, J. Med. Chem., 1988, 31, 697-700. The general method described in Step 1 of Example 1 was used to react 4-chloro-3-nitroquinoline (41.7 g, 200 mmol), ethyl 6-aminocaproate hydrochloride (46.9 g, 240 mmol) and triethylamine (50.6 g, 500 mmol) in dichloromethane for 15 hours to provide ethyl 6-(3-nitroquinolin-4-ylamino)hexanoate (60.6 g) as a yellow solid.

Sources & evidence

ORD record
ord-44c2357cb4954200b6d163113eae4c37
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Reaction notes

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