(6-Bromoisochroman-1-yl)acetic acid → 1-(4-Chlorophenyl)-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-Chlorophenyl)-4-[2-(6-bromoisochroman-1-yl)]acetyl piperazine	HCID 53966005	—
Product	1-(4-Chlorophenyl)-4-[2-(6-bromoisochroman-1-yl)ethyl]piperazine	HCID 23288875	—

Reaction Steps

(6-Bromoisochroman-1-yl)acetic acid (EXAMPLE 22, LXVIII) is coupled with 4-chlorophenylpiperazine (XI) and the resulting amide, 1-(4-chlorophenyl)-4-[2-(6-bromoisochroman-1-yl)]acetyl piperazine (LXIII, 1.39 mmol) is reduced according to the general procedure of EXAMPLE 50 and making non-critical variations, to give the title compound, mp 94-96°; IR (mull) 1500, 1483, 1448, 1248, 1242, 1152, 1144, 1113, 1102, 815 cm-1 ; NMR (300 MHz, CDCl3) 7.32-7.26, 7.19, 6.97, 6.83, 4.78, 4.14-4.07, 3.78-3.69, 3.16, 3.00-2.90, 2.7-2.48, 2.15-1.90; CMR (75 MHz, CDCl3) 149.6, 137.1, 136.0, 131.4, 129.1, 128.7, 126.3, 124.6, 120.0, 116.9, 74.0, 62.6, 54.3, 53.3, 53.0, 48.9, 33.0 and 28.6 δ.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06133446
Source dataset	uspto-grants-2000_10
ORD ID	ord-f3d7eda628e943788e4984882503b16a
Source note	uspto-grants-2000_10