Ammonia → (2R,4S)-2-benzyl-1-(2-naphthylacetyl)-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine

Participants

Role	Name	HCID	Charge
Reactant	Ammonia	HCID 222	—
Reactant	Triethylamine	HCID 8471	—
Reactant	2-Naphthaleneacetic acid	HCID 11393	—
Reactant	1-Chloro-N,N-2-trimethylpropenylamine	HCID 640792	—
Reactant	(2R,4S)-2-Benzyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine	HCID 57202094	—
Solvent	Dichloromethane methanol	HCID 21226129	—
Product	(2R,4S)-2-benzyl-1-(2-naphthylacetyl)-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine	HCID 57233831	—

Reaction Steps

105 mg (0.561 mmol) of 2-naphtylacetic acid are reacted in analogy to Example 6 first 92 μl (0.655 mmol) of 1-chloro-N,N,2-trimethyl-1-propen-1-amine and subsequently with 200 mg (0.468 mmol) of (2R*,4S*)-2-benzyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine and 130 μl (0.936 mmol) of triethylamine to give the product TLC: methylene chloride/methanol/conc. ammonia (700:50:1) Rf =0.56, FD-MS: M+ =595.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05646144
Source dataset	uspto-grants-1997_07
ORD ID	ord-af7fb0b602b241f5bb6bfdd2b94efd73
Source note	uspto-grants-1997_07