Cyclohexylamine → HCID 178461164, compound

HRID 1510148Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C@@:12]3([CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[O:19])[C@@H:14]([CH3:28])[CH2:13]3)[C:11](=[NH:29])[NH:10][C:9]2=[O:30])[CH:5]=[CH:6][CH:7]=1.[CH:31]1(N)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl.CO>[CH:31]1([NH:29][C:11]2[C@:12]3([CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)=[O:19])[C@@H:14]([CH3:28])[CH2:13]3)[N:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)[C:9](=[O:30])[N:10]=2)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

Conditions

Temperature: 110 °C

Procedure

Benzyl (5R,7S)-1-(3-fluorophenyl)-4-imino-7-methyl-2-oxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate (27.2 g, 0.066 moles) was dissolved in 100 mL toluene, cyclohexylamine (60 mL, 0.523 moles) was added and the mixture was heated to 110° C. over the weekend in a 1 L roundbottom flask fitted with a condenser. The reaction was diluted with CHCl3 and MeOH until soluble and washed with 1 Normal HCl three times to remove excess cyclohexylamine. The organic was dried with MgSO4, filtered and concentrated to give the product which was used in the next step without further purification.

Workup

customfitted with a condenser
washwashed with 1 Normal HCl three times
customto remove excess cyclohexylamine
dry with materialThe organic was dried with MgSO4
filtrationfiltered
concentrationconcentrated
customto give the product which
customwas used in the next step without further purification

Sources & evidence

ORD record: ord-1844af2d362945088ec415d29b3541bf
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211904B2

Reaction notes

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