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

Reaction equation

BrC1C=C2C(=CC=1)C(CC(O)=O)OCC2.O.Cl.Cl.C1(CCN2CCN(C3C=CC=CC=3OC)CC2)C2C(=CC=CC=2)CCO1.[F:45][C:46]1[CH:51]=[CH:50][C:49]([N:52]2[CH2:57][CH2:56][N:55]([C:58](=O)[CH2:59][CH:60]3[C:69]4[C:64](=[CH:65][C:66]([Br:70])=[CH:67][CH:68]=4)[CH2:63][CH2:62][O:61]3)[CH2:54][CH2:53]2)=[CH:48][CH:47]=1>>[F:45][C:46]1[CH:51]=[CH:50][C:49]([N:52]2[CH2:53][CH2:54][N:55]([CH2:58][CH2:59][CH:60]3[C:69]4[C:64](=[CH:65][C:66]([Br:70])=[CH:67][CH:68]=4)[CH2:63][CH2:62][O:61]3)[CH2:56][CH2:57]2)=[CH:48][CH:47]=1

Participants

Reactant 3

HCID 10540012(6-Bromoisochroman-1-yl)acetic acid

HCID 232889511-[2-(Isochroman-1-yl)ethyl]-4-(2-methoxyphenyl)piperazine dihydrochloride monohydrate

HCID 538873131-(4-Fluorophenyl)-4-[2-(6-bromoisochroman-1-yl)]acetyl piperazine

Product 1

HCID 154878361-(4-Fluorophenyl)-4-[2-(6-bromoisochroman-1-yl)ethyl]piperazine

Procedure

(6-Bromoisochroman-1-yl)acetic acid (EXAMPLE 22, LXVIII) is coupled with 4-fluorophenylpiperazine (XI) and the resulting amide, 1-(4-fluorophenyl)-4-[2-(6-bromoisochroman-1-yl)]acetyl piperazine (LXIII, 1.64 mmol) is reduced following the general procedure of EXAMPLE 50 and making non-critical variations, to give the title compound, HRMS Calcd for C21H24N2O1Br1F1 =418.1056, found=418.1057.