Triethylamine → HCID 178465556, compound

HRID 427179Notes

Reaction equation

HRID 427179 reaction equation
Cl.Cl.[NH2:3][CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:13][NH2:14])[CH:11]=2)[CH2:6][CH2:5]1.[CH3:15][CH2:16][N:17](CC)CC>CCO>[NH2:14][CH2:13][C:10]1[CH:11]=[C:12]2[C:7]([CH2:6][CH2:5][CH:4]2[NH:3][C:16](=[NH:17])[CH3:15])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 18356551HCID 18356551, compound

Product 1

HCID 178465556HCID 178465556, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

6-Cyanoindan-1-one (prepared using the procedure of Allinger and Jones, JOC 1962, p70. vol 27 for the tetralone analogue) (3.86 g, 24.5 mmol) was converted to the 1-oxime-O-benzyl ether and reduced with BH3-THF by the methods described in example 59 to give 1-amino-6-(aminomethyl)indane. The diamine was isolated in 31% yield as the 2 HCl salt by treatment of an ether solution with 4.0N HCl in dioxane. 1-Amino-6-aminomethylindane 2HCl (0.5 g, 2.1 mmol) was stirred in EtOH (20 ml), cooled to 0° C. and treated with NEt3 (0.59 ml, 4.2 mmol). Intermediate A (0.43 g, 2.1 mmol) was added and the mixture was allowed to warm to 20° C. and stir overnight. The white crystaline product was collected and washed with a small volume of ether and dried in vacuo to give N-(6-(Aminomethyl)-1-indanyl)acetamidine (0.27 g, 35%) as the 2 HCl salt NMR (D2O) 7.45-7.25 (m, 3H), 4.8 (m, 1H), 4.45 (s, 2H), 3.2-2.85 (m, 2H), 2.6)m, 1H), 2.2 (s, 3H, CH3), 2.1 (m, 1H).

Workup

  1. temperatureto warm to 20° C.
  2. customThe white crystaline product was collected
  3. washwashed with a small volume of ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-1c15bff4395c4f4185145415c4bed5d2
Source dataset
uspto-grants-2001_11
Patent number
USRE037438E1

Reaction notes

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