Triethylamine → (2R*,4S*)-2-benzyl-1-(3,5-dichlorobenzoyl)-N-(1-naphthoyl)-4-piperidinamine

HRID 264696Notes

Reaction equation

HRID 264696 reaction equation
[CH2:1]([C@@H:8]1[CH2:13][C@@H:12]([NH2:14])[CH2:11][CH2:10][N:9]1[C:15](=[O:24])[C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]1([C:35](Cl)=[O:36])[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1.C(N(CC)CC)C>>[CH2:1]([C@@H:8]1[CH2:13][C@@H:12]([NH:14][C:35]([C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH:28]=[CH:27][CH:26]=2)=[O:36])[CH2:11][CH2:10][N:9]1[C:15](=[O:24])[C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 701461-Naphthalenecarbonyl chlorideHCID 53839030(2R*,4S*)-2-benzyl-1-(3,5-dichlorobenzoyl)-4-piperidinamine

Product 1

HCID 57114567(2R*,4S*)-2-benzyl-1-(3,5-dichlorobenzoyl)-N-(1-naphthoyl)-4-piperidinamine

Procedure

150 mg (0.431 mmol) of (2R*,4S*)-2-benzyl-1-(3,5-dichlorobenzoyl)-4-piperidinamine are reacted in analogy to Example 39a with 75 μl (0.495 mmol) of 1-naphthoyl chloride and 81 μl (0.578 mmol) of triethylamine. The title compound ##STR89## is obtained (208 mg, 97%) as oil. TLC:methylene chloride/methanol/conc. ammonia (1000:50:1) Rf =0.85, FD-MS:M+ =516, 518; IR:3680, 3400, 1620 cm-1.

Sources & evidence

ORD record
ord-c8e2886686814613bf19d13158d56c61
Source dataset
uspto-grants-1997_07
Patent number
US05646144

Reaction notes

Loading…