1-Carbobenzoxy-4-piperidinecarboxylic Acid → Benzyl 4-((3-chloropyrazin-2-yl)methylcarbamoyl)piperidine-1-carboxylate

HRID 245689Notes

Reaction equation

HRID 245689 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([OH:19])=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(C1CCN(C(OCC2C=CC=CC=2)=O)CC1)=O.Cl.[NH2:40][CH2:41][C:42]1[C:47]([Cl:48])=[N:46][CH:45]=[CH:44][N:43]=1>>[Cl:48][C:47]1[C:42]([CH2:41][NH:40][C:17]([CH:14]2[CH2:13][CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:10])[CH2:16][CH2:15]2)=[O:19])=[N:43][CH:44]=[CH:45][N:46]=1

Participants

4

Reactant 3

HCID 7364891-Carbobenzoxy-4-piperidinecarboxylic AcidHCID 2776270Benzyl 4-(chlorocarbonyl)piperidine-1-carboxylateHCID 42614233(3-Chloropyrazin-2-yl)methanamine hydrochloride

Product 1

HCID 42609366Benzyl 4-((3-chloropyrazin-2-yl)methylcarbamoyl)piperidine-1-carboxylateYield 83.4%

Procedure

Using the procedures described in example 16 step 16a 1-[(benzyloxy)carbonyl]piperidine-4-carboxylic acid (2.5 g) was transformed into 2.75 g of crude benzyl 4-(chlorocarbonyl)piperidine-1-carboxylate and the latter compound was coupled with 2-aminomethyl-3-chloropyrazine hydrochloride (content 77%; 2.28 g) to give benzyl 4-((3-chloropyrazin-2-yl)methylcarbamoyl)piperidine-1-carboxylate (3.08 g) after purification by column chromatography (silica gel, dichloromethane/methanol gradient 100/0 to 90/10).

Sources & evidence

ORD record
ord-a03bbc317db548afb1f4ea8da646b2e7
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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