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

HRID 368862Notes

Reaction equation

HRID 368862 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:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=1[N:54]1[CH2:59][CH2:58][N:57]([C:60](=O)[CH2:61][CH:62]2[C:71]3[C:66](=[CH:67][C:68]([Br:72])=[CH:69][CH:70]=3)[CH2:65][CH2:64][O:63]2)[CH2:56][CH2:55]1)[CH3:46]>>[CH2:45]([O:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=1[N:54]1[CH2:59][CH2:58][N:57]([CH2:60][CH2:61][CH:62]2[C:71]3[C:66](=[CH:67][C:68]([Br:72])=[CH:69][CH:70]=3)[CH2:65][CH2:64][O:63]2)[CH2:56][CH2:55]1)[CH3:46]

Participants

4

Reactant 3

HCID 10540012(6-Bromoisochroman-1-yl)acetic acidHCID 232889511-[2-(Isochroman-1-yl)ethyl]-4-(2-methoxyphenyl)piperazine dihydrochloride monohydrateHCID 700809131-(2-Ethoxyphenyl)-4-[2-(6-bromoisochroman-1-yl)]acetyl piperazine

Product 1

HCID 154878371-(2-Ethoxyphenyl)-4-[2-(6-bromoisochroman-1-yl)ethyl]piperazine

Procedure

(6-Bromoisochroman-1-yl)acetic acid (EXAMPLE 22, LXVIII) is coupled with 2-ethoxyphenylpiperazine (XI) and the resulting amide, 1-(2-ethoxyphenyl)-4-[2-(6-bromoisochroman-1-yl)]acetyl piperazine (LXIII, 3.7 mmol) is reduced following the general procedure of EXAMPLE 50 making non-critical variations, to give the title compound, IR (neat) 2816, 1501, 1480, 1448, 1240, 1143, 1124, 1046, 1110 and 748 cm-1 ; NMR (300 MHz, CDCl3) 7.31-7.26, 7.00-6.90, 6.85-6.83, 4.78, 4.14-4.03, 3.78-3.70, 3.13, 3.00-2.90, 2.13, 1.99, 1.45; CMR (75 MHz, CDCl3) 151.37, 141.19, 137.0, 136.1, 131.5, 129.1, 126.4, 122.5, 120.8, 119.8, 117.9, 112.2, 74.2, 63.4, 62.6, 54.6, 53.5, 50.4, 33.0, 28.7 and 14.8 δ; HRMS Calcd for C23H29N2O2Br1 =444.1413, found=444.1400.

Sources & evidence

ORD record
ord-9c1970f9b769475484f49f42309176ba
Source dataset
uspto-grants-2000_10
Patent number
US06133446

Reaction notes

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