Phenylacetyl chloride → HCID 57233268, compound

HRID 1737027Notes

Reaction equation

[CH2:1]([C@@H:8]1[CH2:13][C@@H:12]([N:14]([CH2:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=[CH:24][CH:23]=2)[C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])[CH2:11][CH2:10][NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:39]1([CH2:45][C:46](Cl)=[O:47])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>>[CH2:1]([C@@H:8]1[CH2:13][C@@H:12]([N:14]([CH2:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=[CH:24][CH:23]=2)[C:15](=[O:20])[C:16]([F:18])([F:19])[F:17])[CH2:11][CH2:10][N:9]1[C:46](=[O:47])[CH2:45][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 7679Phenylacetyl chloride

HCID 8471Triethylamine

HCID 57202094(2R*,4S*)-2-Benzyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine

Product 1

HCID 57233268HCID 57233268, compoundYield 81.5%

Procedure

200 mg (0.468 mmol) of (2R*,4S*)-2-benzyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine are reacted in analogy to Example 35a with 72 μl (0.5 15 mmol) of triethylamine and 62 μl (0.468 mmol) of phenylacetyl chloride to give the title compound (208 mg, 81%). TLC: methylene chloride/methanol/conc. ammonia (700:50:1) Rf =0.54, FD-MS: M+ =545.

Sources & evidence

ORD record: ord-3c344aaf4d3241f18d715aaf9e9ce5e8
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05541195

Reaction notes

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