2-Aminoadamantane hydrochloride → HCID 70795046, compound

HRID 1424614Notes

Reaction equation

HRID 1424614 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:15]=1[C:9]1([CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)[CH2:8][CH:7]2[CH:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18].C1N=CN([C:28]([N:30]2C=N[CH:32]=[CH:31]2)=[O:29])C=1.CCN(C(C)C)C(C)C.Cl.[CH:45]12[CH2:54]C3C[CH:51]([CH2:53][CH:47]([CH2:48]3)[CH:46]1N)[CH2:52]2>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:15]=1[C:9]1([CH2:10][CH2:11][N:12]([C:28](=[O:29])[NH:30][CH:31]3[CH:32]4[CH2:54][CH:45]5[CH2:46][CH:47]([CH2:53][CH:51]3[CH2:52]5)[CH2:48]4)[CH2:13][CH2:14]1)[CH2:8][CH:7]2[CH:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

6

Reactant 4

HCID 253312-Aminoadamantane hydrochlorideHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 58137324HCID 58137324, compound

Product 1

HCID 70795046HCID 70795046, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (±)-ethyl 2-(7-bromo-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)propanoate (160 mg, 0.906 mmol) in dry CH2Cl2 was added CDI (176 mg, 1.08 mmol) and DIEA (1.16 g, 9.06 mmol) at 0° C. under N2. The mixture was stirred for 1 h, and 2-adamantanamine hydrochloride (331 mg, 0.906) in CH2Cl2 was added. The reaction mixture was stirred at rt overnight. The solvent was removed under reduced pressure to leave a residue which was purified by preparative TLC to give (±)-ethyl 2-(7-bromo-1′-(2-adamantylcarbamoyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)propanoate (200 mg, 41%). 1H NMR: (400 MHz, CDCl3): δ=1.11 (s, 3H), 1.22 (s, 3H), 1.26 (m, 3H), 1.45 (m, 2H), 1.52 (m, 3H), 1.73 (m, 4H), 1.85 (m, 7H), 1.95 (s, 2H), 2.44 (m, 2H), 3.02-3.26 (m, 4H), 3.79 (m, 2H), 3.98 (m, 3H), 4.25 (m, 2H), 6.93 (m, 1H), 7.01 (m, 1H), 7.35 (m, 1H).

Workup

  1. stirringThe reaction mixture was stirred at rt overnight
  2. customThe solvent was removed under reduced pressure
  3. customto leave a residue which
  4. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-e84482a241e2487f9b643b5a5ef57142
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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