Diisopropylethylamine → N-[2,3-Bis(4-chlorophenyl)-1-methylpropyl]-1-(4-chlorophenyloxy)-cyclohexanecarboxamide

HRID 30395Notes

Reaction equation

HRID 30395 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH:10]([NH2:12])[CH3:11])=[CH:5][CH:4]=1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]2([C:35](O)=[O:36])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[CH:24][CH:23]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=2)[CH:10]([NH:12][C:35]([C:29]2([O:28][C:25]3[CH:24]=[CH:23][C:22]([Cl:21])=[CH:27][CH:26]=3)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[O:36])[CH3:11])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 205112Cyclohexanecarboxylic acid, 1-(p-chlorophenoxy)-HCID 222704272,3-Bis(4-chlorophenyl)-1-methylpropylamine hydrochloride

Product 1

HCID 10196285N-[2,3-Bis(4-chlorophenyl)-1-methylpropyl]-1-(4-chlorophenyloxy)-cyclohexanecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of N-[2,3-bis(4-chlorophenyl)-1-methylpropyl]-amine hydrochloride (Diastereomer α, Reference Example 1) (60 mg, 0.19 mmol) and 1-(4-chlorophenyloxy)cyclohexanecarboxylic acid (60 mg, 0.24 mmol) in 1 mL of methylene chloride was added N,N-diisopropylethylamine (0.10 mL, 0.58 mmol) and tris(pyrrolindinyl)phosphonium hexafluorophosphate (0.10 g, 0.19 mmol). After stirring at room temperature overnight, the reaction mixture was loaded onto a silica gel column eluted with 6:1 hexane/ether to afford the title compound. 1H NMR (500 MHz, CD3OD): δ 7.22 (d, 2H), 7.19 (d, 2H), 7.03 (d, 2H), 6.99 (d, 2H), 6.91 (d, 2H), 6.71 (d, 2H), 4.24 (m, 1H), 2.99 (dd, 1H), 2.80 (ddd, 1H), 2.63 (dd, 1H), 2.3-1.2 (m, 10H), 0.82 (d, 3H). LC-MS: m/e 530 (M+H)+ (5.0 min).

Workup

  1. washeluted with 6:1 hexane/ether

Sources & evidence

ORD record
ord-14bff60fb2514cf4bc906c8aba1b01e8
Source dataset
uspto-grants-2008_09
Patent number
US07423067B2

Reaction notes

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