1-Phenethylamine → HCID 18317240, compound

HRID 1700125Notes

Reaction equation

CS([C:5]1[N:10]=[C:9]([C:11]2[N:12]=[N:13][C:14]([CH:27]3[CH2:32][CH2:31][N:30]([C:33]([O:35][CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[O:34])[CH2:29][CH2:28]3)=[CH:15][C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)[CH:8]=[CH:7][N:6]=1)(=O)=O.[CH3:43][CH:44]([NH2:51])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>>[CH3:43][CH:44]([NH:51][C:5]1[N:10]=[C:9]([C:11]2[N:12]=[N:13][C:14]([CH:27]3[CH2:28][CH2:29][N:30]([C:33]([O:35][CH2:36][C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)=[O:34])[CH2:31][CH2:32]3)=[CH:15][C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:24])[F:25])[CH:18]=2)[CH:8]=[CH:7][N:6]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

Reactant 2

HCID 74081-Phenethylamine

HCID 18317246HCID 18317246, compound

Product 1

HCID 18317240HCID 18317240, compoundYield 93.9%

Conditions

Temperature: 120 °C

Procedure

Under Ar, a mixture of 28 (0.62 g, 1.0 mmol) and (S) (−)-α-methylbenzylamine (1.5 mL, 11.6 mmol) was heated at 120 ° C. for 3 h. The reaction was chromatographed on a Still column (40 mm) and the product eluted with 80% EtOAc-hexanes to yield 0.6 g of 29.

Workup

customThe reaction was chromatographed on a Still column (40 mm)
washthe product eluted with 80% EtOAc-hexanes

Sources & evidence

ORD record: ord-67856e5c03bf4ed1a0c927119a359364
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06350744B1

Reaction notes

Loading…