N-{5-[1-(3-aminopropyl)-4-piperidinyl]-2-hydroxyphenyl}-2-methylpropanamide → N-(3-[1-(2-aminoethyl)-4-piperidinyl]phenyl)-2-methylpropanamide

HRID 1269149Notes

Reaction equation

HRID 1269149 reaction equation
[NH2:1]CCCN1CCC(C2C=C(NC(=O)N(C)C)C=CC=2)CC1.NCCCN1CCC(C2C=C(NC(=O)OC(C)C)C=CC=2)CC1.NCCCN1CCC(C2C=C(NC(=O)OCC3C=CC=CC=3)C=CC=2)CC1.NC[CH2:75][CH2:76][N:77]1[CH2:82][CH2:81][CH:80]([C:83]2[CH:84]=[C:85]([NH:91][C:92](=[O:96])[CH:93]([CH3:95])[CH3:94])[CH:86]=[CH:87][C:88]=2OC)[CH2:79][CH2:78]1.NCCCN1CCC(C2C=C(NC(=O)CCC)C=CC=2OC)CC1.NCCCN1CCC(C2C=CC(O)=C(NC(=O)C(C)C)C=2)CC1>>[NH2:1][CH2:75][CH2:76][N:77]1[CH2:78][CH2:79][CH:80]([C:83]2[CH:84]=[C:85]([NH:91][C:92](=[O:96])[CH:93]([CH3:94])[CH3:95])[CH:86]=[CH:87][CH:88]=2)[CH2:81][CH2:82]1

Participants

7

Reactant 6

HCID 21957198N-{5-[1-(3-aminopropyl)-4-piperidinyl]-2-hydroxyphenyl}-2-methylpropanamideHCID 21957208Isopropyl 3-[1-(3-aminopropyl)-4-piperidinyl]phenylcarbamateHCID 21957209N-{3-[1-(3-aminopropyl)-4-piperidinyl]-4-methoxyphenyl}-2-methylpropanamideHCID 21957216Benzyl 3-[1-(3-aminopropyl)-4-piperidinyl]phenylcarbamateHCID 21957241N-{3-[1-(3-aminopropyl)4-piperidinyl]4-methoxyphenyl}butanamideHCID 21957254N'-{3-[1-(3-aminopropyl)-4-piperidinyl]phenyl}-N,N-dimethylurea

Product 1

HCID 16757469N-(3-[1-(2-aminoethyl)-4-piperidinyl]phenyl)-2-methylpropanamide

Procedure

Using the methods described above, the following additional intermediates were synthesized. N′-{3-[1-(3-AMINOPROPYL)-4-PIPERIDINYL]PHENYL}-N,N-DIMETHYLUREA: 1H NMR (400 MHz, CD3OD) δ 7.36 (s, 1H), 7.32–7.25 (m, 1H), 7.21 (t, 1H, J=7.9 Hz), 6.92 (d, 1H, J=7 Hz), 3.33 (s, 6H), 3.17–3.07 (m, 2H), 2.75 (t, 2H, J=6,9), 2.58–2.44 (m, 3H), 2.14 (dt, 2H, J=11.8, 2.7 Hz), 1.93–1.67 (m, 8H). ISOPROPYL 3-[1-(3-AMINOPROPYL)-4-PIPERIDINYL]PHENYLCARBAMATE: 1H NMR (400 MHz, CDCl3) δ 7.20 (broad s, 1H), 7.16 (d, 1H, J=5.3 Hz), 7.08 (t, 1H, J=8.3 Hz), 6.80 (d, 1H, J=7.4 Hz), 4.89–4.79 (m, 1H), 3.21 (quintet, 1H, J=1.6 Hz), 3.03–2.95 (m, 2H), 2.61 (t, 2H, 6.8 Hz), 2.46–2.31 (m, 3H), 2.01 (dt, 2H, J=11.7, 2.8 Hz), 1.78–1.57 (m, 7H), 1.19 (d, 6H, J=6.2 Hz). BENZYL 3-[1-(3-AMINOPROPYL)-4-PIPERIDINYL]PHENYLCARBAMATE: 1H NMR (400 MHz, CDCl3) δ 7.60–7.30 (m, 9H), 7.08 (dt, 1H, J=7.5, 1.4 Hz), 5.34 (s, 2H), 4.09 (quintet, 1H, J=5.7 Hz), 3.30–3.10 (m, 4H), 2.65 (t, 2H, J=7.8 Hz), 2.28 (dt, 2H, J=12, 1.4 Hz), 2.07–1.85 (m, 7H). N-{3-[1-(3-AMINOPROPYL)-4-PIPERIDINYL]-4-METHOXYPHENYL}-2-METHYLPROPANAMIDE: ESMS m/e: 334.6 (M+H)+. N-{3-[1-(3-AMINOPROPYL)-4-PIPERIDINYL]-4-METHOXYPHENYL}BUTANAMIDE: 1H NMR (400 MHz, CD3OD) δ 7.46–7.57 (m, 1H), 6.97 (s, 1H), 6.77 (d, 1H, J=8.8 Hz), 3.88–3.80 (m, 2H), 3.78 (s, 3H), 3.12–2.74 (m, 4H), 2.46 (t, 2H, J=6.6 Hz), 2.39 (t, 2H, J=7.3 Hz), 2.07–1.94 (m, 2H), 1.87–1.44 (m, 9H), 1.02 (t, 3H, J=7.4 Hz). N-{5-[1-(3-AMINOPROPYL)-4-PIPERIDINYL]-2-HYDROXYPHENYL}-2-METHYLPROPANAMIDE: 1H NMR (400 MHz, CD3OD) δ 8.12–8.08 (m, 1H), 7.70–7.66 (m, 2H), 7.44 (d, 1H, J=2.2 Hz), 2.79–2.55 (m, 3H), 2.39–2.28 (m, 3H), 2.26 (d, 2H, J=11.6 Hz), 1.98 (dt, 2H, J=12, 2.5 Hz), 1.74–1.53 (m, 6H), 1.11 (d, 6H, J=6.8 Hz).

Workup

  1. customwere synthesized

Sources & evidence

ORD record
ord-ed140f28f8c540adadb42530ba392dc2
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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