Propionyl chloride → 2-methyl-N-(3-{1-[(3S)-3-phenyl-3-(propionylamino)propyl]-4-piperidinyl}phenyl)propanamide

HRID 2087205Notes

Reaction equation

HRID 2087205 reaction equation
[C:1]([NH:4][C@H:5]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[C:16]([NH:20][C:21](=[O:25])[CH:22]([CH3:24])[CH3:23])[CH:17]=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)(=[O:3])[CH3:2].N[C@H:33](C1C=CC=CC=1)CCN1CCC(C2C=C(NC(=O)C(C)C)C=CC=2)CC1.C(Cl)(=O)CC>>[CH3:23][CH:22]([CH3:24])[C:21]([NH:20][C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([CH:11]2[CH2:12][CH2:13][N:8]([CH2:7][CH2:6][C@@H:5]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[NH:4][C:1](=[O:3])[CH2:2][CH3:33])[CH2:9][CH2:10]2)[CH:15]=1)=[O:25]

Participants

4

Reactant 3

HCID 62324Propionyl chlorideHCID 69523292N-(3-{1-[(3S)-3-(acetylamino)-3-phenylpropyl]-4-piperidinyl)phenyl)-2-methylpropanamideHCID 69523474N-(3-(1-[(3S)-3-amino-3-phenylpropyl]-4-piperidinyl)phenyl)-2-methylpropanamide

Product 1

HCID 207229762-methyl-N-(3-{1-[(3S)-3-phenyl-3-(propionylamino)propyl]-4-piperidinyl}phenyl)propanamideYield 97%

Procedure

According to the procedure used for the synthesis of N-(3-{1-[(3S)-3-(acetylamino)-3-phenylpropyl]-4-piperidinyl}phenyl)-2-methylpropanamide, N-(3-{1-[(3S)-3-amino-3-phenylpropyl]-4-piperidinyl}phenyl)-2-methylpropanamide (11.0 mg, 0.0280 mmol) and propionyl chloride (3.80 mg, 0.0420 mmol) provided 2-methyl-N-(3-{1-[(3S)-3-phenyl-3-(propionylamino)propyl]-4-piperidinyl}phenyl)propanamide (12 mg, 97% yield). 1H NMR (400 MHz, CDCl3) δ 8.05 (s, 1H), 7.59 (s, 1H), 7.40-7.20 (m, 7H), 6.96 (s, 1H), 5.19-5.12 (m, 1H), 3.18 (d, 1H, J=12.0 Hz), 2.99 (d, 1H, J=10.4 Hz), 2.93-2.86 (m, 1H), 2.61-2.40 (m, 3H), 2.38-2.23 (m, 3H), 2.19-1.75 (m, 8H), 1.25 (d, 6H, J=6.9 Hz), 1.22-1.08 (m, 3H); ESMS m/e: 436.4 (M+H)+.

Sources & evidence

ORD record
ord-fa9743a797084461b1b97f21cf75a76c
Source dataset
uspto-grants-2004_04
Patent number
US06727264B1

Reaction notes

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