2-(2-Bromophenyl)ethan-1-ol → 1-(4-Methoxyphenyl)-4-[2-(5-bromoisochroman-1-yl)ethyl]piperazine

HRID 1417834

Reaction equation

HRID 1417834 reaction equation
BrC1C=CC=CC=1CCO.BrC1C=CC=C2C=1CCOC2CC(OCC)=O.BrC1C=CC=C2C=1CCOC2CC(O)=O.CON1CCN(C2C=CC=CC=2)CC1.[CH3:57][O:58][C:59]1[CH:64]=[CH:63][C:62]([N:65]2[CH2:70][CH2:69][N:68]([C:71](=O)[CH2:72][CH:73]3[C:82]4[C:77](=[C:78]([Br:83])[CH:79]=[CH:80][CH:81]=4)[CH2:76][CH2:75][O:74]3)[CH2:67][CH2:66]2)=[CH:61][CH:60]=1>>[CH3:57][O:58][C:59]1[CH:60]=[CH:61][C:62]([N:65]2[CH2:70][CH2:69][N:68]([CH2:71][CH2:72][CH:73]3[C:82]4[C:77](=[C:78]([Br:83])[CH:79]=[CH:80][CH:81]=4)[CH2:76][CH2:75][O:74]3)[CH2:67][CH2:66]2)=[CH:63][CH:64]=1

Participants

6

Reactant 5

HCID 27340892-(2-Bromophenyl)ethan-1-olHCID 23170892p-MethoxyphenylpiperazineHCID 23288918Ethyl 2-(5-bromoisochroman-1-yl)acetate2×HCID 232889192-(5-Bromoisochroman-1-yl)acetic acidHCID 571283801-(4-Methoxyphenyl)-4-[2-(5-bromoisochroman-1-yl)]acetyl piperazine

Product 1

HCID 232887441-(4-Methoxyphenyl)-4-[2-(5-bromoisochroman-1-yl)ethyl]piperazine

Procedure

Following the general procedure of EXAMPLE 45 (step 1) and making non-critical variations 2-(o-bromophenyl)-1-ethanol (XLIX, 3.3 g) is converted to ethyl 2-(5-bromoisochroman-1-yl)acetate (LXXI). Following the general procedure of EXAMPLE 45 (Step 2) and making non-critical variations ethyl 2-(5-bromoisochroman-1-yl)acetate (LXXI, 1.0 g) is hydrolyzed to the corresponding acid, 2-(5-bromoisochroman-1-yl)acetic acid (LXXII). This acid (LXXII, 740 mg) is coupled with p-methoxyphenylpiperazine (V) and the resulting amide, 1-(4-methoxyphenyl)-4-[2-(5-bromoisochroman-1-yl)]acetyl piperazine (LXXIII, 1.10 g) is reduced according to the general procedure described in EXAMPLE 50 (making non-critical variations) to give the title compound, mp 105°-106°.

Sources & evidence

ORD record
ord-66dbd11a0b72441d9830134850d5107b
Source dataset
uspto-grants-1999_03
Patent number
US05877317

Linked notes

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