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

HRID 368866Notes

Reaction equation

HRID 368866 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.[CH2:45]([O:49][C:50]1[CH:55]=[CH:54][C:53]([N:56]2[CH2:61][CH2:60][N:59]([C:62](=O)[CH2:63][CH:64]3[C:73]4[C:68](=[CH:69][C:70]([Br:74])=[CH:71][CH:72]=4)[CH2:67][CH2:66][O:65]3)[CH2:58][CH2:57]2)=[CH:52][CH:51]=1)[CH2:46][CH2:47][CH3:48]>>[CH2:45]([O:49][C:50]1[CH:51]=[CH:52][C:53]([N:56]2[CH2:61][CH2:60][N:59]([CH2:62][CH2:63][CH:64]3[C:73]4[C:68](=[CH:69][C:70]([Br:74])=[CH:71][CH:72]=4)[CH2:67][CH2:66][O:65]3)[CH2:58][CH2:57]2)=[CH:54][CH:55]=1)[CH2:46][CH2:47][CH3:48]

Participants

4

Reactant 3

HCID 10540012(6-Bromoisochroman-1-yl)acetic acidHCID 232889511-[2-(Isochroman-1-yl)ethyl]-4-(2-methoxyphenyl)piperazine dihydrochloride monohydrateHCID 538265431-(4-Butyloxyphenyl)-4-[2-(6-bromoisochroman-1-yl)]acetyl piperazine

Product 1

HCID 232887981-(4-Butyloxyphenyl)-4-[2-(6-bromoisochroman-1-yl)ethyl]piperazine

Procedure

(6-Bromoisochroman-1-yl)acetic acid (EXAMPLE 22, LXVIII) is coupled with 4-butyloxyphenylpiperazine (XI) and the resulting amide, 1-(4-butyloxyphenyl)-4-[2-(6-bromoisochroman-1-yl)]acetyl piperazine (LXIII, 4.2 mmol) is reduced according to the general procedure of EXAMPLE 50 making non-critical variations, to give the title compound, NMR (300 MHz, CDCl3) 7.32, 7.06, 6.85, 4.80, 4.13-4.08, 3.71, 3.28, 3.10-2.72, 2.65, 2.40, 2.22, 1.74, 1.46, 1.25 and 0.96 δ.

Sources & evidence

ORD record
ord-cb0f6e21760e4379b7c66b7ffc00902f
Source dataset
uspto-grants-2000_10
Patent number
US06133446

Reaction notes

Loading…