Dichloromethane → Ammonia dichloromethane

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	1-Piperidinepropanol, 2-methyl-	HCID 248806	—
Reactant	Di-tert-butyl diazene-1,2-dicarboxylate	HCID 6034084	—
Reactant	4-Piperidin-1-yl methyl-phenol	HCID 20035992	—
Product	2-Methyl-1-[3-(4-piperidin-1-ylmethyl-phenoxy)-propyl]-piperidine	HCID 9945413	—
Product	Ammonia dichloromethane	HCID 22731429	2.5%

Reaction Steps

A suspension of the product of Example 17 (176 mg), 3-(2-methyl-piperidin-1-yl)-propan-1-ol (145 mg), and polymer supported triphenylphosphine (613 mg; loading: 3 mmol/g) in DCM (5 mL) was treated with di-tert-butylazodicarboxylate (316 mg). After 2 h, the resulting mixture was filtered, and the filtrate was evaporated. Chromatography of the residue (2.5% 2 M methanolic ammonia/DCM) gave the title compound as a colorless oil (60 mg). 1H NMR (400 MHz, CDCl3): 7.20 (d, J=8.6 Hz, 2H), 6.83 (d, J=8.6 Hz, 2H), 4.01–3.92 (m, 2H), 3.40 (s, 2H), 2.90–2.81 (m, 2H), 2.56–2.47 (m, 1H), 2.40–2.25 (m, 5H), 2.21–2.14 (m, 1H), 1.97–1.88 (m, 2H), 1.70–1.51 (m, 8H), 1.45–1.25 (m, 4H), 1.07 (d, J=6.2 Hz, 3H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07186732B2
Source dataset	uspto-grants-2007_03
ORD ID	ord-149af4f2e6354bb1a084c07d98520ec3
Source note	uspto-grants-2007_03