Hydrochloric Acid → Ammonia

HRID 1879918Notes

Reaction equation

HRID 1879918 reaction equation
[N:1]1C=CC=C(CNC(C2(CC3C=CC=CC=3)CCNCC2)=O)C=1.Cl.C(OC([N:32]1[CH2:37][CH2:36][C:35]([CH2:41][C:42]2[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][CH:43]=2)([C:38]([OH:40])=O)[CH2:34][CH2:33]1)=O)(C)(C)C.[CH2:49]([NH2:56])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>>[CH2:49]([NH:56][C:38]([C:35]1([CH2:41][C:42]2[CH:43]=[CH:44][C:45]([Cl:48])=[CH:46][CH:47]=2)[CH2:34][CH2:33][NH:32][CH2:37][CH2:36]1)=[O:40])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1.[NH3:1]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 7504BenzylamineHCID 189689961-(tert-Butoxycarbonyl)-4-[(4-chlorophenyl)methyl]piperidine-4-carboxylic acidHCID 59327480HCID 59327480, compound

Product 2

HCID 222AmmoniaHCID 59327452HCID 59327452, compound

Procedure

In analogy to the procedure described for the synthesis of 4-benzyl-piperidine-4-carboxylic acid (pyridin-3-ylmethyl)-amide; hydrochloride (intermediate 1) the title compound was prepared from 4-(4-chloro-benzyl)-piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (commercially available) and benzylamine (commercially available) with subsequent cleavage of the protecting group under acidic conditions. The title compound was purified on silica eluting with a gradient formed from DCM and 2N NH3 and methanol. MS (m/e): 236.1/343.2 (MH+).

Workup

  1. customThe title compound was purified on silica eluting with a gradient

Sources & evidence

ORD record
ord-613293ea3f204604acc0954c79c9f14e
Source dataset
uspto-grants-2012_11
Patent number
US08318749B2

Reaction notes

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