Acetyl chloride → 1-acetyl-N-(2-adamantyl)spiro[indoline-3,4'-piperidine]-1'-carboxamide

HRID 1424590Notes

Reaction equation

HRID 1424590 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([N:14]1[CH2:19][CH2:18][C:17]3([C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[NH:21][CH2:20]3)[CH2:16][CH2:15]1)=[O:13])[CH2:8]2.CCN(C(C)C)C(C)C.[C:37](Cl)(=[O:39])[CH3:38]>C(Cl)Cl>[C:37]([N:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:17]2([CH2:16][CH2:15][N:14]([C:12]([NH:11][CH:2]3[CH:3]4[CH2:9][CH:7]5[CH2:6][CH:5]([CH2:10][CH:1]3[CH2:8]5)[CH2:4]4)=[O:13])[CH2:19][CH2:18]2)[CH2:20]1)(=[O:39])[CH3:38]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 25067083N-(2-adamantyl)spiro[indoline-3,4'-piperidine]-1'-carboxamide

Product 1

HCID 669536241-acetyl-N-(2-adamantyl)spiro[indoline-3,4'-piperidine]-1'-carboxamideYield 12%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution N-(2-adamantyl)spiro[indoline-3,4′-piperidine]-1′-carboxamide (50 mg, 0.108 mmol) and DIEA (27.86 g, 0.22 mmol) in dry CH2Cl2 (2-mL) at 0° C. under nitrogen was added dropwise a solution of acetyl chloride (9.28 mg, 0.12 mmol) in CH2Cl2 (0.5 mL). The mixture was stirred overnight at rt and evaporated to give a residue, which was purified by preparative HPLC to provide a white solid 1-acetyl-N-(2-adamantyl)spiro[indoline-3,4′-piperidine]-1′-carboxamide (5.2 mg, 12%). 1H NMR (400 MHz, CD3OD): δ=1.61 (s, 1H), 1.653 (d, 2H), 1.72 (s, 1H), 1.88 (m, 10H), 2.015 (d, 5H), 2.286 (s, 3H), 3.027 (t, 2H), 3.867 (s, 1H), 4.088 (d, 4H), 7.044 (t, 1H), 7.191 (t, 2H), 8.082 (d, 1H); LC-MS (4 min) tR=1.59 min, m/z=408(M++1).

Workup

  1. customevaporated
  2. customto give a residue, which
  3. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-a558896d653d4a8dba633cee2ffb34f4
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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