(6-Bromoisochroman-1-yl)acetic acid → 1-(4-Methylphenyl)-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-(4-Methylphenyl)-4-[2-(6-bromoisochroman-1-yl)]acetyl piperazine	HCID 53872319	—
Product	1-(4-Methylphenyl)-4-[2-(6-bromoisochroman-1-yl)ethyl]piperazine	HCID 23288916	—

Reaction Steps

(6-Bromoisochroman-1-yl)acetic acid (EXAMPLE 22, LXVIII) is coupled with 4-methylphenylpiperazine (XI) and the resulting amide, 1-(4-methylphenyl)-4-[2-(6-bromoisochroman-1-yl)]acetyl piperazine (LXIII, 1.49 mmol) is reduced according to the general procedure of EXAMPLE 50 and making non-critical variations, to give the title compound, NMR (300 MHz, CDCl3) 7.32-7.26, 7.07, 6.97, 6.84, 4.78, 4.14-3.07, 3.78-3.69, 3.16, 2.94, 2.7-2.48, 2.26, 2.15-1.90 δ; CMR (75 MHz, CDCl3) 149.0, 136.9, 136.1, 131.4, 129.4, 129.0, 128.9, 126.3, 119.8, 116.1, 74.1, 62.6, 54.4, 53.2, 49.5, 33.0, 28.6 and 20.2 δ.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06133446
Source dataset	uspto-grants-2000_10
ORD ID	ord-082caaba54a1406ea03dbcef3a336bec
Source note	uspto-grants-2000_10