Benzenemethanamine, N-[6-(3-butynyloxy)hexyl]- → 5-((1R)-2-{Benzyl[6-(but-3-ynyloxy)hexyl]amino}-1-hydroxyethyl)-2-(benzyloxy)phenylformamide

Participants

Role	Name	HCID	Charge
Reactant	Benzenemethanamine, N-[6-(3-butynyloxy)hexyl]-	HCID 22145668	—
Reactant	benzyloxy-5-[(2R)-oxiran-2-yl]phenylformamide	HCID 86760081	—
Product	5-((1R)-2-{Benzyl[6-(but-3-ynyloxy)hexyl]amino}-1-hydroxyethyl)-2-(benzyloxy)phenylformamide	HCID 11443930	159.6%

Reaction Steps

A stirred mixture of 2-(benzyloxy-5-[(2R)-oxiran-2-yl]phenylformamide (R Hett et al, Organic Process Research & Development, 1998, 2, 96-99) (8.6 g) and N-benzyl-6-(but-3-ynyloxy)hexan-1-amine (9.1 g) was heated at 120° for 2 h. The mixture was purified by chromatography (Merck 9385) eluting with cyclohexane/ethyl acetate (2:1) to give the title compound (13.47 g). LCMS RT=2.68 min.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07045658B2
Source dataset	uspto-grants-2006_05
ORD ID	ord-f6583bd1abf84b58b96e7dc6bc002542
Source note	uspto-grants-2006_05