(6-Bromoisochroman-1-yl)acetic acid → 1-(2-Ethoxyphenyl)-4-[2-(6-bromoisochroman-1-yl)ethyl]piperazine

Participants

Role	Name	HCID	Charge
Reactant	(6-Bromoisochroman-1-yl)acetic acid	HCID 10540012	—
Reactant	1-[2-(Isochroman-1-yl)ethyl]-4-(2-methoxyphenyl)piperazine dihydrochloride monohydrate	HCID 23288951	—
Reactant	1-(2-Ethoxyphenyl)-4-[2-(6-bromoisochroman-1-yl)]acetyl piperazine	HCID 70080913	—
Product	1-(2-Ethoxyphenyl)-4-[2-(6-bromoisochroman-1-yl)ethyl]piperazine	HCID 15487837	—

Reaction Steps

(6-Bromoisochroman-1-yl)acetic acid (EXAMPLE 22, LXVIII) is coupled with 2-ethoxyphenylpiperazine (XI) and the resulting amide, 1-(2-ethoxyphenyl)-4-[2-(6-bromoisochroman-1-yl)]acetyl piperazine (LXIII, 3.7 mmol) is reduced following the general procedure of EXAMPLE 50 making non-critical variations, to give the title compound, IR (neat) 2816, 1501, 1480, 1448, 1240, 1143, 1124, 1046, 1110 and 748 cm-1 ; NMR (300 MHz, CDCl3) 7.31-7.26, 7.00-6.90, 6.85°6.83, 4.78, 4.14-4.03, 3.78-3.70, 3.13, 3.00-2.90, 2.13, 1.99, 1.45; CMR (75 MHz, CDCl3) 151.37, 141.19, 137.0, 136.1, 131.5, 129.1, 126.4, 122.5, 120.8, 119.8, 117.9, 112.2, 74.2, 63.4, 62.6, 54.6, 53.5, 50.4, 33.0, 28.7 and 14.8δ; HRMS Calcd for C23H29N2O2Br1 =444.1413, found=444.1400.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05877317
Source dataset	uspto-grants-1999_03
ORD ID	ord-3d016ab485244126ad1b3d5b65a661e9
Source note	uspto-grants-1999_03