Diisopropylethylamine → HCID 67360391, compound

HRID 1667147Notes

Reaction equation

HRID 1667147 reaction equation
[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:12][CH2:11][CH2:10][NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:19]=[C:20]1[C:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:24][CH2:23][CH2:22][N:21]1[CH2:38][C:39](O)=[O:40].C(N(C(C)C)CC)(C)C>ClCCl>[C:13]1([C:7]2([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[O:12][CH2:11][CH2:10][N:9]([C:39](=[O:40])[CH2:38][N:21]3[CH2:22][CH2:23][CH2:24][C:25]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:20]3=[O:19])[CH2:8]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 522663HCID 522663, compoundHCID 673592802-(2-Oxo-3,3-diphenylpiperidin-1-yl)acetic acid

Product 1

HCID 67360391HCID 67360391, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2,2-diphenylmorpholine (0.075 g, 0.313 mmol), 2-(2-oxo-3,3-diphenylpiperidin-1-yl)acetic acid (Example 68E, 0.097 g, 0.313 mmol) and 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (0.131 g, 0.345 mmol) in dichloromethane (1 mL) was added diisopropylethylamine (0.082 mL, 0.470 mmol), and the reaction mixture was stirred at room temperature overnight. The reaction was loaded directly onto a silica gel column (Analogix®, SF15-24) and the product was eluted with a gradient of 5% to 100% ethyl acetate/hexanes over 25 minutes with a flow rate of 30 mL/minute. 1H NMR (300 MHz, CDCl3) δ ppm 7.18-7.60 (m, 20H), 4.43 (s, 2H), 3.50-3.70, m, 6H), 3.05-3.10 (m, 2H), 2.40-2.50 (m, 2H), 1.55-1.70 (m, 2H); MS (DCI+) m/z 531 (M+H)+.

Workup

  1. washthe product was eluted with a gradient of 5% to 100% ethyl acetate/hexanes over 25 minutes with a flow rate of 30 mL/minute

Sources & evidence

ORD record
ord-ee4306f2bc6e441e815ae5f9ceb9aa62
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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