1-(Diphenylmethyl)-4-piperidinamine → HCID 54099729, compound

HRID 362928Notes

Reaction equation

HRID 362928 reaction equation
[CH2:1]([NH:8][C:9]1[O:14][C:13](=[O:15])[C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[N:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[NH2:20][CH:21]1[CH2:26][CH2:25][N:24]([CH:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:23][CH2:22]1>C1(C)C=CC=CC=1>[CH2:1]([NH:8][C:9](=[O:14])[NH:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([NH:20][CH:21]1[CH2:26][CH2:25][N:24]([CH:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:23][CH2:22]1)=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 128755351-(Diphenylmethyl)-4-piperidinamineHCID 541699282-(Heptylamino)-4H-3,1-benzoxazin-4-one

Product 1

HCID 54099729HCID 54099729, compoundYield 43.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-n-heptylamino-4H-3,1-benzoxazin-4-one (3.0 g, 10 mmol) and 4-amino-1-diphenylmethylpiperidine (3.0 g, 10 mmol) in toluene (20 ml) was refluxed for 3 hours and then concentrated. The residue was purified by column chromatography on silica gel (20% ethyl acetate in hexane) to give 2-(N'-n-heptylureido)-N-(1-diphenylmethylpiperidin-4-yl)benzamide (2.3 g, 40%): mp 182° C.; 1H NMR (CDCl3)ppm: 0.87 (3H, t), 1.27-1.30 (8H, m), 1.47-1.67 (4H, m), 1.95-2.12 (4H, m), 2.84 (2H, d), 3.24 (2H, q), 3.90-3.94 (1H, m), 4.26 (1H, s), 4.56 (1H, t), 6.09 (1H, d), 6.92-6.98 (1H, m), 7.16-7.44 (12H, m), 8.41 (1H, d), 10.26 (1H, s).

Workup

  1. temperaturewas refluxed for 3 hours
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography on silica gel (20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-2c14145ba42843beb0d5825dc1f78cef
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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