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

HRID 368864Notes

Reaction equation

HRID 368864 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.[Cl: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>>[Cl: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

4

Reactant 3

HCID 10540012(6-Bromoisochroman-1-yl)acetic acidHCID 232889511-[2-(Isochroman-1-yl)ethyl]-4-(2-methoxyphenyl)piperazine dihydrochloride monohydrateHCID 539660051-(4-Chlorophenyl)-4-[2-(6-bromoisochroman-1-yl)]acetyl piperazine

Product 1

HCID 232888751-(4-Chlorophenyl)-4-[2-(6-bromoisochroman-1-yl)ethyl]piperazine

Procedure

(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.

Sources & evidence

ORD record
ord-f3d7eda628e943788e4984882503b16a
Source dataset
uspto-grants-2000_10
Patent number
US06133446

Reaction notes

Loading…