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

HRID 368863Notes

Reaction equation

HRID 368863 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.[CH3:45][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>>[CH3:45][C:46]1[CH:47]=[CH:48][C:49]([N:52]2[CH2:57][CH2:56][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)[CH2:54][CH2:53]2)=[CH:50][CH:51]=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 538723191-(4-Methylphenyl)-4-[2-(6-bromoisochroman-1-yl)]acetyl piperazine

Product 1

HCID 232889161-(4-Methylphenyl)-4-[2-(6-bromoisochroman-1-yl)ethyl]piperazine

Procedure

(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.

Sources & evidence

ORD record
ord-082caaba54a1406ea03dbcef3a336bec
Source dataset
uspto-grants-2000_10
Patent number
US06133446

Reaction notes

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