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

HRID 368865Notes

Reaction equation

HRID 368865 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:52][C:53]1[CH:58]=[CH:57][C:56]([N:59]2[CH2:64][CH2:63][N:62]([C:65](=O)[CH2:66][CH:67]3[C:76]4[C:71](=[CH:72][C:73]([Br:77])=[CH:74][CH:75]=4)[CH2:70][CH2:69][O:68]3)[CH2:61][CH2:60]2)=[CH:55][CH:54]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>>[CH2:45]([O:52][C:53]1[CH:54]=[CH:55][C:56]([N:59]2[CH2:64][CH2:63][N:62]([CH2:65][CH2:66][CH:67]3[C:76]4[C:71](=[CH:72][C:73]([Br:77])=[CH:74][CH:75]=4)[CH2:70][CH2:69][O:68]3)[CH2:61][CH2:60]2)=[CH:57][CH:58]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[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 571324891-(4-Benzyloxyphenyl)-4-[2-(6-bromoisochroman-1-yl)]acetyl piperazine

Product 1

HCID 158590331-(4-Benzyloxyphenyl)-4-[2-(6-bromoisochroman-1-yl)ethyl]piperazine

Procedure

(6-Bromoisochroman-1-yl)acetic acid (EXAMPLE 22, LXVIII) is coupled with 4-benzyloxyphenylpiperazine (XI) and the resulting amide, 1-(4-benzyloxyphenyl)-4-[2-(6-bromoisochroman-1-yl)]acetyl piperazine (LXIII, 7.23 mmol) is reduced according to the general procedure of EXAMPLE 50 and making non-critical variations to give the title compound, mp 87-90°.

Sources & evidence

ORD record
ord-e12012a1f11a4036b1642eed119e57fb
Source dataset
uspto-grants-2000_10
Patent number
US06133446

Reaction notes

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